As filed with the Securities and Exchange Commission on May 26, 2004.

                                                           Registration No. 333-

================================================================================

                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM S-3
                             REGISTRATION STATEMENT

                        UNDER THE SECURITIES ACT OF 1933

                         WINTRUST FINANCIAL CORPORATION
             (Exact Name of Registrant as Specified in its Charter)




                                                                                       

                                                      727 NORTH BANK LANE
                                                LAKE FOREST, ILLINOIS 60045-1951
                                                         (847) 615-4096
              ILLINOIS                (Address, Including Zip Code, and Telephone Number,          36-3873352
    (State or Other Jurisdiction         Including Area Code, of Registrant's Principal           (IRS Employer
 of Incorporation or Organization)                     Executive Offices)                    Identification Number)


                                DAVID A. DYKSTRA
           SENIOR EXECUTIVE VICE PRESIDENT AND CHIEF OPERATING OFFICER
                               727 NORTH BANK LANE
                        LAKE FOREST, ILLINOIS 60045-1951
                                 (847) 615-4096

            (Name, Address, Including Zip Code, and Telephone Number,
                   Including Area Code, of Agent for Service)

      The Commission is requested to send copies of all communications to:

                           JENNIFER DURHAM KING, ESQ.
                     VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C.
                            222 NORTH LASALLE STREET
                          CHICAGO, ILLINOIS 60601-1003
                                 (312) 609-7500

         Approximate date of commencement of proposed sale to the public: From
time to time after this Registration Statement becomes effective.
         If the only securities being registered on this Form are being offered
pursuant to dividend or interest reinvestment plans, check the following box.
/ /
         If any of the securities being registered on this Form are to be
offered on a delayed or continuous basis pursuant to Rule 415 under the
Securities Act of 1933, other than securities offered only in connection with
dividend or interest reinvestment plans, check the following box. /X/
         If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, check the following box and
list the Securities Act registration statement number of the earlier effective
registration statement for the same offering. / /
         If this Form is a post-effective amendment filed pursuant to Rule
462(c) under the Securities Act, check the following box and list the Securities
Act registration statement number of the earlier effective registration
statement for the same offering. / /
         If delivery of the prospectus is expected to be made pursuant to Rule
434, please check the following box. / /
                                 _______________

                         CALCULATION OF REGISTRATION FEE



                                                                                                    
=================================================================================================================================
                                                                                         Proposed Maximum
      Title of Each Class of          Amount to be     Proposed Maximum Offering        Aggregate Offering         Amount of
    Securities to be Registered       Registered(1)      Price Per Share (1)(2)              Price(1)           Registration Fee
---------------------------------------------------------------------------------------------------------------------------------
Common Stock, without par value*        275,000                $45.86                    $12,611,500               $1,598
=================================================================================================================================

*       Including the preferred share purchase rights associated therewith.
(1)     Includes 180,438 shares newly issued to the selling shareholders as part
        of the consideration paid by the Registrant in connection with two
        recent acquisitions and 94,562 shares that may be issued to the selling
        shareholders as part of contingent consideration that may become payable
        over the next five years depending on attainment of certain performance
        criteria.
(2)     Estimated solely for the purpose of determining the registration fee
        pursuant to Rule 457(c), based on the average of the high and low sale
        prices on May 20, 2004, as reported on the Nasdaq National Market, of
        $46.20 and $45.52, respectively.



                                 _______________

         THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE
OR DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT
SHALL FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF
THE SECURITIES ACT OF 1933 OR UNTIL THE REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTION 8(A),
MAY DETERMINE.

================================================================================



The information in this prospectus is not complete and may be changed. We may
not sell these securities until the registration statement filed with the
Securities and Exchange Commission is effective. This prospectus is not an offer
to sell these securities and it is not soliciting an offer to buy these
securities in any state where the offer or sale is not permitted.

                   Subject to completion, dated May 26, 2004.

PROSPECTUS

                         WINTRUST FINANCIAL CORPORATION

                         275,000 SHARES OF COMMON STOCK


         Certain shareholders of Wintrust Financial Corporation are offering for
sale from time to time up to 275,000 shares of our common stock under this
prospectus. The selling shareholders may offer the shares:

         o        to or through one or more underwriters;

         o        directly to purchasers;

         o        on the Nasdaq National Market in typical brokerage
                  transactions;

         o        in negotiated transactions, or otherwise.

         The selling shareholders may sell the shares of common stock covered by
this prospectus:

         o        at market prices prevailing at the time of sale;

         o        at prices related to the then-prevailing market price; or

         o        at negotiated prices.

         We will not receive any proceeds from the sale of the shares of common
stock by the selling shareholders. No minimum purchase is required and no
arrangement has been made to have funds received by the selling shareholders
and/or any registered representatives placed in an escrow, trust or similar
account or arrangement.

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC." On May 25, 2004, the closing price of our common stock as
reported on Nasdaq was $47.95 per share.

         YOU SHOULD CONSIDER, AMONG OTHER THINGS, THE INFORMATION SET FORTH IN
THE "RISK FACTORS" SECTION BEGINNING ON PAGE 6 OF THIS PROSPECTUS.

         THE SHARES OF COMMON STOCK THAT ARE BEING OFFERED ARE NOT SAVINGS
ACCOUNTS OR DEPOSITS OR OTHER OBLIGATIONS OF A BANK AND ARE NOT INSURED OR
GUARANTEED BY THE BANK INSURANCE FUND OR THE FEDERAL DEPOSIT INSURANCE
CORPORATION OR ANY GOVERNMENTAL AGENCY.

         NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES
COMMISSION HAS APPROVED OR DISAPPROVED OF THESE SECURITIES OR DETERMINED IF THIS
PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A
CRIMINAL OFFENSE.





               The date of this prospectus is ____________, 2004.



                                TABLE OF CONTENTS

                                                                            PAGE

Summary Information............................................................1
Risk Factors...................................................................6
Use of Proceeds...............................................................12
Price Range of Common Stock and Dividend Policy...............................12
Selling Shareholders..........................................................13
Plan of Distribution..........................................................15
Transfer Agent................................................................16
Legal Matters.................................................................16
Experts  .....................................................................16
Where You Can Find More Information...........................................16
Documents Incorporated by Reference...........................................17

                            ------------------------

         The information in this prospectus is complete and accurate as of the
date on the front cover, but the information may have changed since that date.
You should carefully consider the information provided in and incorporated by
reference in this prospectus. We have not authorized any other person to provide
you with different information. This prospectus is not an offer to sell, nor is
it seeking an offer to buy, these securities in any state where the offer or
sale is not permitted.

                SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

         We make certain forward-looking statements in this prospectus that are
based upon our current expectations and projections about current events. We
intend these forward-looking statements to be covered by the safe harbor
provisions for forward-looking statements contained in the Private Securities
Litigation Reform Act of 1995, and we are including this statement for purposes
of these safe harbor provisions. You can identify these statements from our use
of the words "may," "will," "should," "could," "would," "plan," "potential,"
"estimate," "project," "believe," "intend," "anticipate," "expect," "target" and
similar expressions. These forward-looking statements include statements
relating to:

         o        our goals, intentions and expectations;

         o        our business plans and growth strategies; and

         o        estimates of our risks and future costs and benefits.

         Forward-looking statements are subject to significant risks,
assumptions and uncertainties, including among other things, changes in general
economic and business conditions and the risks and other factors set forth in
the "Risk Factors" section beginning on page 6.

         Because of these and other uncertainties, our actual future results,
performance or achievements, or industry results, may be materially different
from the results indicated by forward-looking statements. In addition, our past
results of operations do not necessarily indicate our future results. You should
not place undue reliance on any forward-looking statement, which speak only as
of the date they were made. We may not update these forward-looking statements,
even though our situation may change in the future, unless we are obligated to
do so under the federal securities laws. We qualify all of our forward-looking
statements by these cautionary statements.

                                       i



                               SUMMARY INFORMATION

         This summary highlights information about Wintrust and our business and
should be read in conjunction with the documents incorporated by reference into
this prospectus. Because this is a summary, it may not contain all of the
information that is important to you. Therefore, you should also read the more
detailed information that is included in the documents incorporated by
reference, as well as the "Risk Factors" section of this prospectus beginning on
page 6, before making a decision to invest in our common stock.

       This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 275,000 shares of common
stock. We newly issued 180,438 of these shares on May 19, 2004 to the selling
shareholders in connection with our acquisitions of SGB Corporation and Guardian
Real Estate Services, Inc. As part of the acquisition of SGB Corporation, we
paid $10.8 million in cash to the selling shareholders. We also agreed to pay
additional consideration contingent upon the attainment of certain performance
measures over the next five years. This prospectus covers up to 94,562
additional shares that we may issue to the selling shareholders if they become
eligible to receive additional purchase price amounts. Because we were not
required to register the issuance of shares in these transactions with the SEC,
the selling shareholders have "restricted stock." We are registering the shares
to enable the selling shareholders to resell the shares in the public market
from time to time or on a delayed basis and to permit secondary trading of the
shares after they are sold by the selling shareholders.

       All of the selling shareholders were the former owners of SGB Corporation
and Guardian, and each of them is currently employed by us pursuant to
employment agreements entered into in connection with the transaction.

ABOUT WINTRUST FINANCIAL CORPORATION

         We are a financial holding company headquartered in Lake Forest,
Illinois, with total assets of approximately $5.0 billion at March 31, 2004. We
currently operate ten community banks, all located in the Chicago metropolitan
area, which provide community-oriented, personal and commercial banking services
primarily to individuals and small to mid-size businesses through 40 banking
facilities as of April 30, 2004. Each of our banks provides a full complement of
commercial and consumer loan and deposit products and services. We provide
wealth management services through our trust company, investment adviser and
broker-dealer subsidiaries to customers primarily located in the Midwest, as
well as to customers of our banks. In addition, we are involved in specialty
lending through operating subsidiaries or divisions of certain of our banks. Our
specialty lending niches include commercial insurance premium finance; accounts
receivable financing and administrative services to the temporary staffing
industry; and indirect auto lending in which we purchase loans through
Chicago-area automobile dealerships.

COMMUNITY BANKING

         We have developed our community banking franchise through the formation
of de novo banks, the opening of branch offices of the banks and acquisitions.
Of our 10 banking subsidiaries, eight are de novo banks organized by us or our
management team and two are banks we acquired within the past year that were
started by others in 1995 and 2001. Our first bank was organized in December
1991, and in early April 2004, we opened our tenth bank subsidiary, Beverly Bank
& Trust Company, N.A., on the southwest side of Chicago to service the Beverly
Hills/Morgan Park communities as well as the surrounding communities of
Evergreen Park and Merrionette Park. On May 10, 2004, we announced the signing
of a definitive agreement to acquire Northview Financial Corporation, the parent
company of Northview Bank and Trust, with locations in Northfield, Mundelein and
Wheaton, Illinois. We expect this transaction to close late in the third quarter
of 2004.



         We have grown from $1.1 billion in assets at December 31, 1997 to
approximately $5.0 billion in assets at March 31, 2004. Our financial
performance has been affected by costs associated with growing market share in
deposits and loans, establishing and acquiring new banks and opening new branch
facilities, and building an experienced management team. Our recent financial
performance generally reflects the improved profitability of our operating
subsidiaries as they mature, offset by the costs of establishing and acquiring
new banks and opening new branch facilities. Our experience has been that it
generally takes 13 to 24 months for new banks to first achieve operational
profitability depending on the number and timing of branch facilities added.

WEALTH MANAGEMENT SERVICES

         We currently offer a full range of wealth management services through
four separate subsidiaries, including trust and investment services, asset
management and securities brokerage services marketed primarily under the Wayne
Hummer name. We acquired the Wayne Hummer operations, based in the Chicago area,
in February 2002. Wayne Hummer Investments, our broker-dealer subsidiary, has
been in operation since 1931.

         Through Wayne Hummer Trust Company we offer trust and investment
services to existing bank customers and are also targeting small to mid-size
businesses and affluent individuals whose needs command the personalized
attention offered by our experienced trust professionals. Assets under
administration at the trust company were approximately $600.6 million at March
31, 2004.

         Through Wayne Hummer Investments, a registered broker-dealer, we
provide a full range of private client and securities brokerage services to
clients located primarily in the Midwest. Client assets at the brokerage firm
were approximately $4.8 billion at March 31, 2004. Focused Investments, LLC, a
broker-dealer and wholly-owned subsidiary of Wayne Hummer Investments, provides
a full range of investment services to individuals through a network of
relationships with community-based financial institutions primarily in Illinois.

         Through Wayne Hummer Asset Management Company, a registered investment
adviser, we provide money management services and advisory services to
individuals and institutional, municipal and tax-exempt organizations as well as
three proprietary mutual funds, and also provides portfolio management and
financial supervision for a wide range of pension and profit-sharing plans. At
March 31, 2004, individual accounts managed by Wayne Hummer Asset Management
Company totaled approximately $817.9 million, while the three managed mutual
funds had approximately $188.0 million in total assets.

SPECIALTY LENDING

         We conduct our specialty lending businesses through indirect non-bank
subsidiaries and divisions of our banks.

         Through First Insurance Funding, our most significant specialized
lending niche, we make loans to businesses to finance the insurance premiums
they pay on their commercial insurance policies. The loans are originated by
First Insurance Funding working through independent medium and large insurance
agents and brokers located throughout the United States. The insurance premiums
we finance are primarily for commercial customers' purchases of liability,
property and casualty and other commercial insurance. This lending involves
relatively rapid turnover of the loan portfolio and high volume of loan
originations. Because of the indirect nature of this lending and because the
borrowers are located nationwide, this segment may be more susceptible to third
party fraud. The majority of these loans are purchased by our banks in order to
more fully utilize their lending capacity. These loans generally provide the
banks higher yields than alternative investments. Since the second quarter of
1999,

                                       2



we have also been selling some of the loan originations to an unrelated
third party with servicing retained. We sold approximately $90 million, or 13%,
of the receivables generated during the first quarter of 2004. The purchasers of
the loans have limited recourse rights against us if they suffer losses
associated with the loans we sold.

         Through Tricom, Inc. we provide high-yielding, short-term accounts
receivable financing and value-added, outsourced administrative services, such
as data processing of payrolls, billing and cash management services to the
temporary staffing industry. Tricom's clients, located throughout the United
States, provide staffing services to businesses in diversified industries.
During 2003, Tricom processed payrolls with associated client billings of
approximately $305 million and contributed $7.8 million of revenues, net of
interest expense, to us.

         We engage in other specialty lending through divisions of our banks,
including indirect auto lending, medical and municipal equipment leasing, small
aircraft lending, mortgage broker warehouse lending and loans to condominium,
homeowner and community associations. These other specialty loans and leases
together comprised approximately 9.1% of our loan and lease portfolio at March
31, 2004.

         We continue to pursue the development and/or acquisition of other
specialty lending businesses that generate assets suitable for bank investment
and/or secondary market sales. On May 19, 2004, we acquired SGB Corporation
d/b/a WestAmerica Mortgage Company and WestAmerica's affiliate, Guardian Real
Estate Services, Inc. WestAmerica engages primarily in the origination and
purchase of residential mortgages for sale into the secondary market, and
Guardian provides document preparation and other loan closing services to
WestAmerica and its mortgage broker affiliates. We expect our acquisition of
these firms will allow us to enhance the loan origination and document system
and improve the mortgage product offerings of our banks, will further augment
and diversify our revenue stream and will provide additional earning assets as
well as further diversification of our earning asset base.

OPERATIONAL STRATEGY

         Since our first bank was opened in 1991, we have been committed to the
same fundamental operational strategy, the key elements of which include the
following:

         o        MAINTAINING DECISION-MAKING AUTHORITY LOCALLY WITHIN EACH OF
                  OUR OPERATING SUBSIDIARIES AND PROVIDING A HIGH LEVEL OF
                  PERSONAL AND PROFESSIONAL SERVICE. Our community banking
                  philosophy is driven by our emphasis on local independence and
                  decision-making authority within each of our banks. While
                  senior management of Wintrust provides expertise to each of
                  our subsidiaries in the areas of capital planning, long-term
                  strategic planning, marketing and advertising, financial
                  management, investment and asset/liability management, and
                  technology, the separate management teams of each of the
                  banks, as well as First Insurance, Wayne Hummer Trust Company,
                  Tricom, the Wayne Hummer Companies, WestAmerica and Guardian
                  have full managerial responsibilities for customer service and
                  the ongoing day-to-day operations of their respective
                  organizations, subject to the oversight of our Board of
                  Directors and the boards of our subsidiaries. Our operating
                  subsidiaries enjoy the competitive advantages of being able to
                  tailor products and services to meet the differing needs of
                  the customers that they serve, to quickly make decisions
                  affecting customers, and to participate actively in their
                  communities.

         o        EMPLOYING FEWER, BUT HIGHLY QUALIFIED AND PRODUCTIVE
                  INDIVIDUALS AT RELATIVELY HIGH COMPENSATION RATES AND FOCUSING
                  ON LOW NET OVERHEAD RATIOS. Key to our growth and
                  profitability is our management's extensive experience in
                  providing community banking and financial services, and
                  retaining highly qualified managers is critical to our
                  strategy. Our banks' presidents and chief executive officers
                  were selected not only for their years of

                                       3



                  banking experience but also for their business development
                  skills and their strong ties to the communities they serve.
                  Although our management compensation levels may be relatively
                  high, we believe our organizational structure allows us to
                  continue to improve and maintain favorable net overhead ratios
                  as the banks, First Insurance, Wayne Hummer Trust Company and
                  Tricom mature.

         o        MARKETING COMPETITIVE DEPOSIT AND LOAN PRODUCTS. Each of our
                  banks has developed a strong customer base within its
                  communities through the utilization of innovative
                  community-oriented marketing programs. Our banks market their
                  products aggressively through creative newspaper and other
                  advertising, special promotions and frequently sponsored
                  community events. While competitive pricing may create
                  pressure on our net interest margin at times, to be more
                  responsive to the needs of consumers in their specific
                  markets, the banks have also introduced a variety of deposit
                  and loan products to appeal to the unique needs of different
                  types of bank customers, such as different age groups and
                  other special segments of the target markets. Each of our
                  banks has a large board of directors comprised of experienced
                  business persons and other individuals prominent within their
                  respective communities who assist the banking officers with
                  business development.

         o        PURSUING A NUMBER OF SPECIALTY LENDING NICHES. We currently
                  finance loans in several different specialty lending niches to
                  more fully utilize our lending capacity, to diversify our loan
                  portfolio, and to enhance the profitability of our banks. In
                  addition to premium finance loans originated by First
                  Insurance, short-term accounts receivables financed by Tricom,
                  and indirect auto loans, we also engage in mortgage warehouse
                  lending, medical and municipal equipment leasing, homeowners
                  and condominium association lending and small aircraft
                  lending. Loans in our specialty lending niches tend to be
                  higher yielding than other commercial and consumer loans in
                  our banks' portfolios, but may involve greater credit risks
                  than generally associated with loan portfolios of more
                  traditional community banks due to marketability of the
                  collateral or because we do not have direct customer
                  relationships with the underlying borrowers.

         o        FOCUS ON GENERATING FEE INCOME TO AUGMENT NET INTEREST INCOME.
                  During 2003 and the first quarter of 2004, we generated fee
                  income from a variety of sources including the origination and
                  sale of mortgage loans, account service charges, trust, asset
                  management and brokerage fees, premium income from selling
                  covered call option contracts on fixed income securities we
                  own, as well as gains on sales of premium finance receivables
                  and securities. In addition, we earn administrative fees at
                  Tricom related to its payroll processing business.
                  Non-interest income as a percentage of net revenues was 38%
                  for the years ended December 31, 2003 and 2002, and was 34%
                  for the first three months of 2004.

GROWTH STRATEGY

         Key elements of our growth strategy include the following:

         o        INTERNAL GROWTH OF OUR EXISTING BANKS. Due to our de novo
                  strategy, we believe we have not yet realized the full deposit
                  and asset generation potential in the communities now served
                  by our existing banking facilities. We believe we can leverage
                  our existing infrastructure to support additional business
                  while maintaining a high level of personalized customer
                  service and responsiveness. As consolidation and the trend
                  toward nationwide franchises continue in the financial
                  services industry, management expects that more individuals
                  and small businesses will become disenchanted with the
                  perceived lower level of service offered by the larger
                  institutions, providing continuing market share opportunity
                  for us. We may from time to time compete for deposits,
                  particularly in our newer markets, with aggressive pricing,

                                       4



                  which may reduce our net interest margin. With management's
                  focus on balancing further asset growth with earnings growth,
                  our current strategy is to continue less aggressive deposit
                  pricing at those banks with significant market share and more
                  established customer bases.

         o        EXPANDING INTO ATTRACTIVE MARKETS WITH LIMITED LOCAL BANKING
                  COMPETITION. We plan to continue our geographic expansion by
                  leveraging our existing banks and opening new branch
                  facilities in nearby communities where management believes
                  targeted customers would be attracted to a community banking
                  alternative. We have plans to add seven new branches of our
                  existing banks over the next 12 months. We also intend to
                  continue the formation of additional de novo banks in
                  attractive markets in and around the Chicago metropolitan
                  area. We will continue to be impacted by start-up costs to the
                  extent we undertake additional de novo bank and branch
                  formations.

                  In addition, part of our strategy is to continue to pursue
                  potential acquisitions of other community-oriented banks that
                  are already operating in desirable markets in the greater
                  Chicago metropolitan area not currently served by our existing
                  banks. For example, we recently announced the signing of a
                  definitive agreement to acquire Northview Financial
                  Corporation, the parent company of Northview Bank and Trust.
                  Acquisitions may have a short-term dilutive effect on earnings
                  per share, although the pending acquisition of Northview is
                  not expected to have any material impact on 2004 earnings per
                  share.

         o        AUGMENTING THE LOAN PORTFOLIO WITH OUR SPECIALTY LENDING
                  NICHES TO ALLOW THE BANKS TO MORE FULLY UTILIZE THEIR LENDING
                  CAPACITY AND ADDING RELATED FINANCIAL SERVICES BUSINESSES TO
                  INCREASE FEE INCOME. Our specialty lending niches have
                  enhanced the profitability of our community banks by
                  optimizing their earning asset base and allowing them to
                  diversify their loan portfolios. We plan to continue to build
                  our sales staff at First Insurance to further increase loan
                  volume in our premium finance business, seeking to increase
                  our market penetration in selected geographic markets. We may
                  pursue acquisitions or development of additional specialty
                  lending businesses engaged in asset generation suitable for
                  bank investment and/or secondary market sales. We may also
                  pursue acquisitions or development of related financial
                  services businesses to augment fee income, such as our recent
                  acquisition of WestAmerica Mortgage Company and Guardian Real
                  Estate Services, Inc. Management intends to continue to
                  explore various commercial and consumer finance activities and
                  to seek attractive potential acquisition candidates.
                  Acquisitions could have a short-term dilutive effect on
                  earnings per share.

         o        GROWTH OF WEALTH MANAGEMENT SERVICES PROVIDED TO SMALL AND
                  MID-SIZED BUSINESSES AND AFFLUENT INDIVIDUALS. As part of our
                  strategy to build and grow our wealth management business, we
                  are continuing to recruit talented brokers, cross-market our
                  expanded base of brokerage and investment management products
                  and services to our banking clients while offering trust
                  services and estate planning products, as well as traditional
                  banking services, to wealth management customers.

OFFICE LOCATION

         Our principal executive offices are located at 727 North Bank Lane,
Lake Forest, Illinois 60045-1951, and our telephone number is (847) 615-4096.

                                       5



                                  RISK FACTORS

         You should carefully consider the following risk factors before you
decide to buy our common stock. You should also consider the other information
in this prospectus, as well as the documents incorporated by reference in this
prospectus.

DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT OUR PROFITABILITY.

         Our financial results have been and will continue to be impacted by our
strategy of de novo bank formations and branch openings. We have employed this
strategy to build an infrastructure that management believes can support
additional internal growth in our banks' respective markets. We opened our
eighth de novo bank in April 2004, and expect to undertake additional de novo
bank formations or branch openings as we expand into additional communities in
and around Chicago. Based on our experience, management believes that it
generally takes from 13 to 24 months for new banks to first achieve operational
profitability, depending on the number of branch facilities opened, the impact
of organizational and overhead expenses, the start-up phase of generating
deposits and the time lag typically involved in redeploying deposits into
attractively priced loans and other higher yielding earning assets. However, it
may take longer than expected or than the amount of time we have historically
experienced for new banks and/or branch facilities to reach profitability, and
there can be no guarantee that these new banks or branches will ever be
profitable. To the extent we undertake additional de novo bank, branch and
business formations, our level of reported net income, return on average equity
and return on average assets will be impacted by start-up costs associated with
such operations, and we are likely to continue to experience the effects of
higher expenses relative to operating income from the new operations. These
expenses may be higher than we expected or than our experience has shown.

WE COULD ENCOUNTER DIFFICULTIES OR UNEXPECTED DEVELOPMENTS RELATED TO OUR RECENT
AND ANY FUTURE ACQUISITIONS.

         We recently completed our acquisition of WestAmerica and Guardian, and
are currently in the process of integrating that business into our organization.
While we expect this process will go smoothly, to the extent we experience any
significant difficulties or challenges with this integration, our business may
be adversely impacted.

         Our pending acquisition of Northview Financial is subject to bank
regulatory approval as well as approval of Northview's shareholders. While we
currently expect to close the transaction late in the third quarter of 2004,
subject to receipt of these approvals, we may not be successful in completing
the acquisition as planned if, for example, all of the closing conditions are
not met. If we do complete the acquisition, we may be adversely impacted if we
have difficulty integrating the bank into our organization or if the composition
or quality of the bank's assets or liabilities that we acquire differ
significantly from our expectations. In addition, our net income and earnings
per share could be adversely impacted if we incur greater than anticipated costs
associated with operating this bank, if we have difficulty retaining key
personnel at the bank, or if we are unable to grow the business of the bank as
contemplated.

         We plan to continue to pursue potential acquisitions of other
community-oriented banks as well as additional specialty lending and related
financial services businesses which could also present challenges relating to
the integration of the operations of acquired businesses into our organization.
To the extent acquisitions divert a significant amount of management time and
attention, our business could be disrupted.

                                       6



WE DEPEND ON OUR ABILITY TO ATTRACT AND RETAIN KEY PERSONNEL; WE RELY HEAVILY ON
OUR MANAGEMENT TEAM, AND THE UNEXPECTED LOSS OF KEY MANAGERS MAY ADVERSELY
AFFECT OUR OPERATIONS.

         Our success to date has been influenced strongly by our ability to
attract and to retain senior management experienced in banking and financial
services. Retention of senior managers and appropriate succession planning will
continue to be critical to the successful implementation of our strategies. We
have entered into 72 employment contracts with our executive officers and
certain senior officers who we consider to be key employees. It is also
important as we grow to be able to attract and retain additional qualified
senior and middle management. We maintain a limited number of key-man life
insurance policies and maintain bank-owned life insurance policies on most of
our executive and senior officers to offset liabilities under employment
contracts. The unexpected loss of services of any key management personnel, or
the inability to recruit and retain qualified personnel in the future, could
have an adverse effect on our business and financial results.

OUR ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB LOSSES THAT
MAY OCCUR IN OUR LOAN PORTFOLIO.

         Our allowance for loan losses is established in consultation with
management of our operating subsidiaries and is maintained at a level considered
adequate by management to absorb loan and lease losses that are inherent in the
portfolios. At March 31, 2004, our allowance for loan losses was 133.53% of
total non-performing loans and 0.78% of total loans. The amount of future losses
is susceptible to changes in economic, operating and other conditions, including
changes in interest rates, that may be beyond our control, and such losses may
exceed current estimates. Rapidly growing and de novo bank loan portfolios are,
by their nature, unseasoned. As a result, estimating loan loss allowances for
our newer banks is more difficult, and therefore the banks may be more
susceptible to changes in loss estimates, and to losses exceeding estimates,
than banks with more seasoned loan portfolios. Although management believes that
the allowance for loan losses is adequate to absorb losses that may develop in
our existing portfolios of loans and leases, there can be no assurance that the
allowance will prove sufficient to cover actual loan or lease losses in the
future.

OUR PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND COULD EXPOSE
US TO SIGNIFICANT LOSSES.

         Of our total loans at March 31, 2004, 23%, or $783.7 million, were
comprised of commercial insurance premium finance receivables that we generated
through First Insurance. These loans, intended to enhance the average yield of
earning assets of our banks, involve a different, and possibly higher, level of
risk of delinquency or collection than generally associated with loan portfolios
of more traditional community banks. First Insurance also faces unique
operational and internal control challenges due to the relatively rapid turnover
of the premium finance loan portfolio and high volume of new loan originations.
The average term to maturity of these loans is less than 12 months, and the
average loan size when originated is approximately $30,000.

         Because we conduct lending in this segment primarily through
relationships with a large number of unaffiliated insurance agents and because
the borrowers are located nationwide, risk management and general supervisory
oversight may be more difficult than in our banks. We may also be more
susceptible to third party fraud. Acts of fraud are difficult to detect and
deter, and we cannot assure investors that our risk management procedures and
controls will prevent losses from fraudulent activity. For example, in the third
quarter of 2000, we recorded a non-recurring after-tax charge of $2.6 million in
connection with a series of fraudulent loan transactions perpetrated against
First Insurance by one independent insurance agency located in Florida. Although
we have since enhanced our internal control system at First Insurance, we may
continue to be exposed to the risk of significant loss in our premium finance
business.

                                       7



         Due to continued growth in origination volume of premium finance
receivables, since the second quarter of 1999, we have been selling some of the
loans First Insurance originates to an unrelated third party. We have recognized
gains on the sales of the receivables, and the proceeds of sales have provided
us with additional liquidity. Consistent with our strategy to be asset driven,
we expect to pursue similar sales of premium finance receivables in the future;
however, we cannot assure you that there will continue to be a market for sale
of these loans and the extent of our future sales of these loans will depend on
the level of new volume growth in relation to our capacity to retain the loans
within our subsidiary banks' loan portfolios. Because we have a recourse
obligation to the purchaser of premium finance loans that we sell, we could
incur losses in connection with the loans sold if collections on the underlying
loans prove to be insufficient to repay to the purchaser the principal amount of
the loans sold plus interest at the negotiated buy-rate and if the collection
shortfall on the loans sold exceeds our estimate of losses at the time of sale.

OUR STRATEGY OF PURSUING SPECIALTY LENDING NICHES MAY EXPOSE US TO CREDIT RISKS
THAT ARE UNIQUE FOR A COMMUNITY BANKING ORGANIZATION OF OUR SIZE.

         At March 31, 2004, 32.4% of our total loan portfolio consisted of loans
we make in what we consider to be specialty lending niches. In addition to our
premium finance loans, we engage in indirect auto lending, accounts receivable
financing, mortgage broker warehouse lending, loans to condominium, homeowner
and community associations, and to a much lesser extent, medical and municipal
equipment leasing and small aircraft lending.

         Our portfolio of automobile loans are originated indirectly through
unaffiliated automobile dealers located throughout the Chicago metropolitan
area. At March 31, 2004, our indirect auto loans were $177.6 million and
comprised approximately 5% of our loan portfolio. Because we are lending through
third-party originators, our indirect auto portfolio may be relatively riskier
than direct consumer lending. Also, because the indirect auto loan industry is
highly competitive, the cost of collection and repossession of the underlying
collateral may significantly reduce the profitability of this portfolio,
particularly in a recessionary environment.

         Through Tricom we finance payrolls of companies engaged in the
temporary staffing business. At March 31, 2004, these finance receivables
totaled of $23.1 million and represented approximately 1% of our loan portfolio.
The principal source of repayments on the loans we make in this niche are
payments to our borrowers from their customers who are located throughout the
United States. While we employ lockboxes and other cash management techniques to
protect our interests, to the extent third parties fail to pay or fraudulently
engage in the conversion of funds through misuse or nonuse of the lockbox or the
creation of ghost payrolls, we may suffer losses.

         Our lease financing niche may involve a higher degree of credit risk
than mortgage or consumer lending due primarily to the potential for relatively
rapid depreciation of medical equipment and other assets securing leases.
Similarly, in the event of a default of loans originated in our aircraft lending
program, the marketability of the collateral may make it more difficult to
convert this collateral to cash, especially in an adverse economic environment.
In our condominium and homeowner association lending niche, we may face
difficulties in securing repayment from our association borrowers to the extent
they are unable to collect assessments from their members, and we may suffer
losses if we are unable to enforce liens against homeowner properties.

OUR WEALTH MANAGEMENT BUSINESSES ARE VULNERABLE TO FLUCTUATIONS IN THE TRADING
VOLUME AND PRICE LEVELS OF SECURITIES; WE FACE STRONG COMPETITION FOR NEW
BROKERS WE SEEK TO HIRE.

         The results of our wealth management subsidiaries depend heavily on
conditions in the financial markets and on economic conditions generally, both
domestically and abroad. Because currently a

                                       8



significant portion of our revenue in these businesses is derived from
commissions, margin interest revenue and principal transactions, further
declines in stock prices, trading volumes or liquidity could result in the
failure of buyers and sellers of securities to fulfill their settlement
obligations, and in the failure of our brokerage clients to fulfill their credit
obligations, which could adversely affect our profitability.

         The success of the strategy we are pursuing to grow our wealth
management business is largely dependent on our ability to identify, hire and
retain talented securities brokers with investment services experience. We face
strong competition for qualified brokers, and many potential candidates are
subject to restrictive covenants with existing employers. If we are unable to
significantly increase the size of our investment services sales force as
planned, we may have difficulty attracting new accounts and increasing assets
under management and may be unable to improve the profitability of this segment
of our business.

WE MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES.

         Our interest income and interest expense are affected by general
economic conditions and by the policies of regulatory authorities, including the
monetary policies of the Federal Reserve. Changes in interest rates may
influence the growth rate of loans and deposits, the quality of the loan
portfolio, loan and deposit pricing, the volume of loan originations in our
mortgage banking business and the value that we can recognize on the sale of
mortgage loans in the secondary market. We expect the success of WestAmerica,
our newly acquired mortgage banking business, in selling loans into the
secondary market at a gain will be impacted during periods of rising interest
rates. While we have taken measures intended to manage the risks of operating in
a changing interest rate environment, there can be no assurance that such
measures will be effective in avoiding undue interest rate risk. If market
interest rates should move contrary to our "gap" position on interest earning
assets and interest bearing liabilities, the "gap" will work against us and our
net interest income may be negatively affected.

         The success of our covered call option program, which we have used in
effect to hedge our interest rate risk, may also be affected by changes in
interest rates. With the decline in interest rates over the last three years to
historically low levels, we have been able to augment the total return of our
investment securities portfolio by selling call options on fixed-income
securities we own. We recorded fee income of $7.9 million during 2003 compared
to $6.0 million in 2002, from premiums earned on these covered call option
transactions. During the first quarter of 2004, we recorded fee income of $2.2
million on these transactions. In a rising interest rate environment,
particularly if the yield curve remains steep, the amount of premium income we
earn on these transactions will likely decline. Our opportunities to sell
covered call options may be limited in the future if rates continue to rise.

OUR FUTURE SUCCESS IS DEPENDENT ON OUR ABILITY TO COMPETE EFFECTIVELY IN THE
HIGHLY COMPETITIVE BANKING INDUSTRY.

         The financial services business is highly competitive, and we encounter
strong direct competition for deposits, loans and other financial services in
all of our market areas. In recent years, several major bank holding companies
have entered or expanded into the Chicago metropolitan market, and are pursuing
aggressive branching initiatives in the area. Generally, these financial
institutions are significantly larger than we are and have greater access to
capital and other resources. Our ability to compete effectively in the
marketplace is also dependent on our ability to adapt successfully to
technological changes within the banking and financial services industries.

OUR BUSINESS MAY BE ADVERSELY AFFECTED BY THE HIGHLY REGULATED ENVIRONMENT IN
WHICH WE OPERATE.

         We are subject to extensive federal and state legislation, regulation
and supervision. The burden of regulatory compliance has increased under current
legislation and banking regulations and is likely to

                                       9



continue to have or may have a significant impact on the financial services
industry. Recent legislative and regulatory changes, as well as changes in
regulatory enforcement policies and capital adequacy guidelines, are increasing
our costs of doing business and, as a result, may create an advantage for our
competitors who may not be subject to similar legislative and regulatory
requirements. In addition, future regulatory changes, including changes to
regulatory capital requirements, could have an adverse impact on our future
results. Self regulatory organizations, such as the New York Stock Exchange and
the National Association of Securities Dealers, require our securities brokerage
subsidiaries to comply with extensive rules and regulations, and we could be
adversely affected by applicable changes in these regulations.

SINCE OUR BUSINESS IS CONCENTRATED IN THE CHICAGO METROPOLITAN AREA, A DOWNTURN
IN THE CHICAGO ECONOMY MAY ADVERSELY AFFECT OUR BUSINESS.

         Currently, our lending and deposit gathering activities are
concentrated primarily in the greater Chicago metropolitan area. Our success
depends on the general economic condition of Chicago and its surrounding areas.
Declining economic conditions could reduce our growth rate, impair our ability
to collect loans, and generally affect our financial condition and results of
operations.

THERE IS FLUCTUATION IN THE TRADING MARKET FOR OUR COMMON STOCK; YOU MAY NOT BE
ABLE TO RESELL SHARES AT OR ABOVE THE PRICE YOU PAY FOR THEM.

         The price of our common stock has been, and will likely continue to be,
subject to fluctuations based on, among other things, economic and market
conditions for financial services companies and the stock market in general, as
well as changes in investor perceptions of our company.

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The maintenance of an active public trading market depends,
however, upon the existence of willing buyers and sellers, the presence of which
is beyond our control or the control of any market maker, and there can be no
assurance that you will be able to resell shares at or above the price you pay
for them. A number of shares of our common stock are covered by resale
registration statements in addition to the shares offered hereby. We estimate
that there are currently up to approximately 800,000 of those shares outstanding
that have not yet been resold. These remaining shares may be freely sold from
time to time in the market. The market price of our common stock could drop
significantly if shareholders sell or are perceived by the market as intending
to sell large blocks of our shares. In addition, we have plans to issue up to a
maximum of approximately 625,000 shares in our pending acquisition of Northview
Financial, expected to close late in the third quarter of 2004, the majority of
which will be freely tradeable when issued.

OUR SHAREHOLDER RIGHTS PLAN AND PROVISIONS IN OUR ARTICLES OF INCORPORATION AND
OUR BY-LAWS MAY DELAY OR PREVENT AN ACQUISITION OF US BY A THIRD PARTY.

         Our board of directors has implemented a shareholder rights plan. The
rights, which are attached to our shares and trade together with our common
stock, have certain anti-takeover effects. The plan may discourage or make it
more difficult for another party to complete a merger or tender offer for our
shares without negotiating with our board of directors or to launch a proxy
contest or to acquire control of a larger block of our shares. If triggered, the
rights will cause substantial dilution to a person or group that attempts to
acquire us without approval of our board of directors, and under certain
circumstances, the rights beneficially owned by the person or group may become
void. The plan also may have the effect of limiting shareholder participation in
certain transactions such as mergers or tender offers whether or not such
transactions are favored by incumbent directors and key management. In addition,
our executive officers may be more likely to retain their positions with us as a
result of the plan, even if their removal would be beneficial to shareholders
generally.

                                       10



         Our articles of incorporation and our by-laws contain provisions,
including a staggered board provision, that make it more difficult for a third
party to gain control or acquire us without the consent of our board of
directors. These provisions also could discourage proxy contests and may make it
more difficult for dissident shareholders to elect representatives as directors
and take other corporate actions.

         These provisions of our governing documents may have the effect of
delaying, deferring or preventing a transaction or a change in control that
might be in the best interest of our shareholders.

                                       11



                                 USE OF PROCEEDS

         We will not receive any of the proceeds from the sale of the shares of
common stock by the selling shareholders. We expect to incur expenses in
connection with this offering in the amount of approximately $30,000 for
registration, legal, accounting and miscellaneous fees and expenses. We will not
pay for expenses such as commissions and discounts of brokers, dealers or agents
or the fees and expenses of counsel, if any, for the selling shareholders. See
"Selling Shareholders" and "Plan of Distribution."

                 PRICE RANGE OF COMMON STOCK AND DIVIDEND POLICY

         Our common stock is traded on the Nasdaq National Market under the
symbol "WTFC". The following table sets forth the high and low sales prices
reported on the Nasdaq National Market for our common stock for the periods
indicated and the semi-annual dividends paid by us during such periods. The
following information gives effect to a 3-for-2 stock split effective as of
March 14, 2002.




                                             HIGH              LOW           DIVIDEND
                                             ----              ---           --------
                                                                    
2004
----
First Quarter.......................         $50.10           $45.61           $0.100
Second Quarter (through May 25,
   2004)............................          50.44            41.85              --

2003
----
First Quarter.......................         $33.65           $27.19           $0.08
Second Quarter......................          32.40            27.74              --
Third Quarter.......................          38.89            29.30            0.08
Fourth Quarter......................          46.85            37.64              --

2002
----
First Quarter.......................         $22.99           $18.33           $0.06
Second Quarter......................          34.58            22.22              --
Third Quarter.......................          36.00            26.54            0.06
Fourth Quarter......................          32.66            25.45              --


         As of May 25, 2004, there were 1,335 shareholders of record of our
common stock.

DIVIDEND POLICY

         In January 2000, our board of directors approved the payment of our
first semi-annual cash dividend on our common stock. We have continued to pay a
semi-annual cash dividend since that time. The final determination of timing,
amount and payment of dividends on our common stock is at the discretion of our
board of directors and will depend upon our profitability, financial condition,
capital requirements and other relevant factors, including the restrictions
described below. We continue to target an earnings retention ratio of
approximately 90% to support our continued growth.

         Because the principal source of our income at the holding company level
is dividends from our banks, our ability to pay dividends on common stock in the
future may be largely dependent on the banks' ability to pay dividends to us.
Any payment of dividends by the banks is subject to certain restrictions imposed
by federal and state banking laws and regulations.

         Our ability to pay cash dividends on our common stock is also subject
to statutory restrictions and restrictions arising under the terms of our
outstanding and any future debt securities and trust preferred

                                       12



securities. The terms of such securities generally restrict payment of dividends
on common stock until required payments and distributions are made on those
securities and may impose additional restrictions in the future. Under
applicable corporate law, we are permitted to pay dividends only to the extent
of our shareholders' equity. Federal regulation of bank holding companies may
also impose restrictions on the ability of a bank holding company to pay
dividends.

                              SELLING SHAREHOLDERS

         This prospectus relates to the offer and sale from time to time by the
selling shareholders named in this prospectus of up to 275,000 shares of common
stock. We newly issued 180,438 of these shares to the selling shareholders on
May 19, 2004 in connection with our acquisition of SGB Corporation and Guardian
from them. As part of the acquisition of SGB, we paid $10.8 million in cash to
the selling shareholders.

         In connection with the acquisition of both companies, we also agreed to
pay additional consideration contingent upon the attainment of certain
performance measures over the next five years. In each case, this additional
consideration is payable in cash unless, in the case of our acquisition of
Guardian, the payment of any portion of such payments would cause the merger not
to be treated as a reorganization under Section 368(a) of the Internal Revenue
Code of 1986, as amended, in which case the balance of the cash payments due
will be paid through the issuance of shares. Accordingly, this prospectus also
covers up to a total of 94,562 additional shares that may be issuable to the
selling shareholders if they are eligible to receive these additional purchase
price amounts.

         The three selling shareholders were the former owners of SGB
Corporation and Guardian, who together received all of the merger consideration
we paid in the two transactions. We have agreed to continue to employ each of
them as executive officers of SGB Corporation pursuant to the terms of
employment agreements entered into with them in connection with the transaction.

         Because the issuance of the shares in each of the transactions was not
registered with the SEC, the selling shareholders have "restricted stock." We
are registering the shares to enable the selling shareholders to resell the
shares in the public market from time to time or on a delayed basis and to
permit secondary trading of the shares after they are sold by the selling
shareholders. We are paying for the registration of such securities but will not
pay for the fees, commissions, and other similar expenses, if any, of the
selling shareholders, their attorneys or other representatives, as a result of
the sale of such securities by the selling shareholders. See "Use of Proceeds"
and "Plan of Distribution."

                                       13



         The following table sets forth, to the best of our knowledge,
information concerning the selling shareholders, the number of shares to be
offered and sold by the selling shareholders and the amount of common stock that
will be owned by the selling shareholders following the offering (assuming the
sale of all the shares of common stock being offered hereby).




                               NUMBER OF
                              SHARES OWNED                            NUMBER OF SHARES      PERCENTAGE OF SHARES
                                PRIOR TO        NUMBER OF SHARES     TO BE OWNED AFTER       TO BE OWNED AFTER
   SELLING SHAREHOLDER          OFFERING        TO BE OFFERED(1)          OFFERING                OFFERING
   -------------------          --------        ----------------     -----------------      --------------------
                                                                                
Laurence J. Bryar......           60,146               60,146               --                       *
Richard P. George......           60,146               60,146               --                       *
Robert J. Santostefano.           60,146               60,146               --                       *
                                 -------              -------             ------                   -----
   Total...............          180,438              180,438               --                       *
                                 =======              =======             ======                   =====

------------------
*       Less than 1%
(1)     Excludes an aggregate of 94,562 additional shares also covered by this
        prospectus, up to all of which may be issued to the selling shareholders
        in certain circumstances if they are eligible to receive additional
        purchase price amounts that are contingent upon the financial
        performance of Guardian over the next five years. If any such additional
        shares are issued by us, the selling shareholders may offer and sell
        them pursuant hereto in addition to the shares shown in the table above.



                                       14



                              PLAN OF DISTRIBUTION

         The common stock offered by this prospectus may be offered and sold
from time to time by the selling shareholders. As used in this prospectus,
"selling shareholders" includes those individuals or entities who may have had
shares of common stock given to them as a gift by a named selling shareholder
after the date of this prospectus and any individuals or entities who may have
shares of common stock pledged to them as collateral by a named selling
shareholder after the date of this prospectus. If we are notified by a selling
shareholder that a donee or pledgee intends to sell more than 500 shares, a
supplement to this prospectus will be filed naming any donee or pledgee offering
the shares before such a sale is permissible under this prospectus.

         The shares of common stock covered by this prospectus may be sold, from
time to time, by the selling shareholders in one or more types of transactions
(which may include block transactions) on Nasdaq, in the over-the-counter
market, in negotiated transactions, through put or call options transactions
relating to the shares of common stock, through short sales of shares of common
stock, or a combination of such methods of sale, or otherwise at prices and at
terms then prevailing or at prices related to the then current market price, or
in negotiated transactions. The shares of common stock may be sold by one or
more of the following methods: (a) a block trade in which the broker or dealer
so engaged will attempt to sell the shares of common stock as agent but may
position and resell a portion of the block as principal in order to facilitate
the transaction; (b) a purchase by a broker or dealer as principal, and the
resale by such broker or dealer for its account pursuant to this prospectus,
including resale to another broker or dealer; or (c) ordinary brokerage
transactions and transactions in which the broker solicits purchasers. Thus, the
period of distribution of these shares of common stock may occur over an
extended period of time.

         The selling shareholders may effect such transactions by selling the
shares of common stock directly to purchasers or to or through a broker or
dealer, who may act as an agent or principal. Such broker or dealer may receive
compensation in the form of discounts, concessions, or commissions from the
selling shareholders and/or the purchasers of shares of common stock for whom
such broker or dealer may act as agent or to whom he sells as principal, or both
(which compensation as to a particular broker or dealer might be in excess of
customary commissions). We know of no existing agreements, understandings or
arrangements between any selling shareholder, broker, dealer, underwriter or
agent relating to the sale or distribution of the shares of common stock. In
offering the securities, the selling shareholders and any broker-dealers and any
other participating broker-dealers who execute sales for the selling
shareholders may be deemed to be "underwriters" within the meaning of Section
2(11) of the Securities Act of 1933 in connection with such sales, and any
profits realized by the selling shareholders and the compensation of such
broker-dealers may be deemed to be underwriting discounts and commissions.

         The selling shareholders will not pay any of the proceeds from the sale
of the shares of common stock to us. We expect to incur expenses in connection
with this offering in the amount of approximately $30,000 for registration,
legal, accounting and miscellaneous fees and expenses. The selling shareholders
will be solely responsible for commissions and discounts of brokers, dealers or
agents, other selling expenses and the fees and expenses of their own counsel,
if any, none of which will be borne by us.

         Any shares covered by this prospectus which qualify for sale pursuant
to Rule 144 may be sold by the selling shareholders under Rule 144 rather than
pursuant to this prospectus.

         We have informed the selling shareholders that while they are selling
the securities, they (1) are required to comply with Regulation M under the
Securities Exchange Act of 1934 (as described in more detail below), (2) may not
engage in any stabilization activity, except as permitted under the Exchange
Act, (3) are required to furnish each broker-dealer (who may offer this common
stock) copies of this

                                       15



prospectus, and (4) may not bid for or purchase any securities of Wintrust or
attempt to induce any person to purchase any such securities except as permitted
under the Exchange Act.

         Regulation M under the Exchange Act prohibits, with certain exceptions,
participants in a distribution from bidding for or purchasing, for an account in
which the participant has a beneficial interest, any of the securities that are
the subject of the distribution. Regulation M also governs bids and purchases
made in order to stabilize the price of a security in connection with a
distribution of the security.

                                 TRANSFER AGENT

         The transfer agent for our common stock is Illinois Stock Transfer
Company, 209 West Jackson Boulevard, Suite 903, Chicago, Illinois 60606.

                                  LEGAL MATTERS

         Certain legal matters relating to the common stock offered by this
prospectus have been passed upon for us by Vedder, Price, Kaufman & Kammholz,
P.C., Chicago, Illinois.

                                     EXPERTS

         Ernst & Young LLP, independent auditors, have audited our consolidated
financial statements included in our Annual Report on Form 10-K for the year
ended December 31, 2003, as set forth in their report, which is incorporated by
reference in this prospectus. Our financial statements are incorporated by
reference in reliance on Ernst & Young LLP's report, given on their authority as
experts in accounting and auditing.

                       WHERE YOU CAN FIND MORE INFORMATION

         This prospectus is a part of a Registration Statement on Form S-3 that
we filed with the SEC under the Securities Act. This prospectus does not contain
all the information set forth in the registration statement, certain parts of
which are omitted in accordance with the rules and regulations of the SEC. For
further information with respect to us and the securities offered by this
prospectus, reference is made to the registration statement, including the
exhibits to the registration statement and the documents incorporated by
reference.

         We file annual, quarterly and special reports, proxy statements and
other information with the SEC. Our filings are available to the public over the
Internet at the SEC's web site at http://www.sec.gov. You may also read and copy
any document we file with the SEC at its public reference facilities at 450
Fifth Street, N.W., Washington, D.C. 20549. You can also obtain copies of the
documents at prescribed rates by writing to the Public Reference Section of the
SEC at 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at
1-800-SEC-0330 for further information on the operation of the public reference
facilities. Our SEC filings are also available on our web site at
http://www.wintrust.com, and at the office of the Nasdaq National Market. For
further information on obtaining copies of our public filings at the Nasdaq
National Market, you should call (212) 656-5060.

                                       16



                       DOCUMENTS INCORPORATED BY REFERENCE

         We "incorporate by reference" into this prospectus the information we
file with the SEC, which means that we can disclose important information to you
by referring you to those documents. The information incorporated by reference
is an important part of this prospectus.

         Some information contained in this prospectus updates and supersedes
the information incorporated by reference and some information that we file
subsequently with the SEC will automatically update this prospectus. We
incorporate by reference the documents listed below:

         o        our Annual Report on Form 10-K for the fiscal year ended
                  December 31, 2003, filed with the SEC on March 15, 2004 (File
                  No. 0-21923);

         o        our Quarterly Report on Form 10-Q for the quarter ended March
                  31, 2004, filed with the SEC on May 10, 2004 (File No.
                  0-21923);

         o        our Current Report on Form 8-K filed with the SEC on January
                  21, 2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on April 20,
                  2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 5,
                  2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 11,
                  2004 (File No. 0-21923);

         o        our Current Report on Form 8-K filed with the SEC on May 20,
                  2004 (File No. 0-21923); and

         o        the descriptions of (a) our Common Stock contained in our
                  Registration Statement on Form 8-A dated January 3, 1997 (File
                  No. 0-21923), and (b) the associated preferred share purchase
                  rights contained in our Registration Statement on Form 8-A
                  dated August 28, 1998 (File No. 0-21923).

         We also incorporate by reference any filings we make with the SEC under
Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934 after
the initial filing of the registration statement that contains this prospectus
and before the time that all of the shares offered by this prospectus are sold.

         You may request, either orally or in writing, and we will provide, a
copy of these filings at no cost by contacting David A. Dykstra, our Chief
Operating Officer, at the following address and phone number:

         Wintrust Financial Corporation
         727 North Bank Lane
         Lake Forest, Illinois 60045-1951
         (847) 615-4096

                                       17



                                     PART II
                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION

         The following table sets forth the various expenses payable in
connection with the sale and distribution of the securities being registered.
All of such expenses will be paid by Wintrust. All of the amounts shown are
estimates, except for the SEC registration fee. We do not expect our expenses in
connection with this offering to exceed $30,000.

SEC registration fee..................       $ 1,598
Accounting fees and expenses..........         5,000
Legal fees............................        15,000
Miscellaneous.........................         8,402
                                             -------
    Total.............................       $30,000
                                             =======

ITEM 15.  INDEMNIFICATION OF DIRECTORS AND OFFICERS

         In accordance with the Illinois Business Corporation Act (being Chapter
805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of the
Registrant's Certificate of Incorporation provide as follows:

         ARTICLE EIGHT: No director of the corporation shall be liable to the
corporation or its shareholders for monetary damages for breach of fiduciary
duty as a director except for liability (a) for any breach of the director's
duty of loyalty to the corporation or its shareholders, (b) for acts or
omissions not in good faith or that involve intentional misconduct of a knowing
violation of law, (c) under Section 8.65 of the BCA, as the same exists or
hereafter may be amended, or (d) for any transaction from which the director
derived an improper personal benefit.

         ARTICLE NINE, PARAGRAPH 1: The corporation shall indemnify, to the full
extent that it shall have power under applicable law to do so and in a manner
permitted by such law, any person made or threatened to be made a party to any
threatened, pending or completed action, suit or proceeding, whether civil,
criminal, administrative or investigative, by reason of the fact that he or she
is or was a director, officer, employee or agent of the corporation, or who is
or was serving at the request of the corporation as a director, officer,
employee or agent of another corporation, partnership, joint venture, trust or
other enterprise against liabilities and expenses reasonably incurred or paid by
such person in connection with such action, suit or proceeding. The corporation
may indemnify, to the full extent that it shall have power under applicable law
to do so and in a manner permitted by such law, any person made or threatened to
be made a party to any threatened, pending or completed action, suit or
proceeding, whether civil, criminal, administrative or investigative, by reason
of the fact that he or she is or was a director, officer, employee or agent of
the corporation, or is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise against liabilities and expenses reasonably
incurred or paid by such person in connection with such action, suit or
proceeding. The words "liabilities" and "expenses" shall include, without
limitation: liabilities, losses, damages, judgments, fines, penalties, amounts
paid in settlement, expenses, attorneys' fees and costs. Expenses incurred in
defending a civil, criminal, administrative, investigative or other action, suit
or proceeding may be paid by the corporation in advance of the final disposition
of such action, suit or proceeding in accordance with the provisions of Section
8.75 of the BCA.

         The indemnification and advancement of expenses provided by this
Article shall not be deemed exclusive of any other rights to which any person
indemnified may be entitled under any statute, by-law, agreement, vote of
shareholders, or disinterested directors or otherwise, both as to action in his
official

                                      II-1



capacity and as to action in any other capacity while holding such office, and
shall continue as to a person who has ceased to be such director, officer,
employee or agent and shall inure to the benefit of the heirs, executors and
administrators of such person.

         PARAGRAPH 2: The corporation may purchase and maintain insurance on
behalf of any person referred to in the preceding paragraph against any
liability asserted against him or her and incurred by him or her in any such
capacity, or arising out of his or her status as such, whether or not the
corporation would have the power to indemnify him or her against such liability
under the provisions of this Article or otherwise.

         PARAGRAPH 3: For purposes of this Article, references to "the
corporation" shall include, in addition to the resulting corporation, any
constituent corporation (including any constituent of a constituent) absorbed in
a consolidation or merger which, if its separate existence had continued, would
have had power and authority to indemnify its directors, officers, employees or
agents, so that any person who is or was a director, officer, employee or agent
of such constituent corporation, or is or was serving at the request of such
constituent corporation as a director, officer, employee or agent of another
corporation, partnership, joint venture, trust or other enterprise, shall stand
in the same position under the provisions of this Article with respect to the
resulting or surviving corporation as he or she would have with respect to such
constituent corporation if its separate existence had continued.

         PARAGRAPH 4: The provisions of this Article shall be deemed to be a
contract between the corporation and each director or officer who serves in any
such capacity at any time while this Article and the relevant provisions of the
BCA, or other applicable law, if any, are in effect, and any repeal or
modification of any such law or of this Article shall not affect any rights or
obligations then existing with respect to any state of facts then or theretofore
existing or any action, suit or proceeding theretofore or thereafter brought or
threatened based in whole or in part upon any such state of facts.

         PARAGRAPH 5: For purposes of this Article, references to "other
enterprises" shall include employee benefit plans; references to "fines" shall
include any excise taxes assessed on a person with respect to any employee
benefit plan; and references to "serving at the request of the corporation"
shall include any service as a director, officer, employee or agent of the
corporation which imposes duties on, or involves services by, such director,
officer, employee or agent with respect to any employee benefit plan, its
participants, or beneficiaries; and a person who acted in good faith and in a
manner he or she reasonably believed to be in the interest of the participants
and beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner not opposed to the best interests of the corporation.

         Section 6.3 of the Registrant's By-laws provides as follows:

         SECTION 6.3. MANDATORY INDEMNIFICATION. To the extent that a director,
officer, employee or agent of a corporation, or any subsidiary or subsidiaries,
as the case may be, has been successful on the merits or otherwise in defense of
any action, suit or proceeding referred to in Sections 6.1 and 6.2, or in
defense of any claim, issue or matter therein, such person shall be indemnified
against expenses (including attorneys' fees) actually and reasonably incurred by
him or her in connection therewith.

         The Illinois Business Corporation Act provides for indemnification of
officers, directors, employees and agents as follows:

         5/8.75 INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS;
INSURANCE. (a) A corporation may indemnify any person who was or is a party, or
is threatened to be made a party to any threatened, pending or completed action,
suit or proceeding, whether civil, criminal, administrative or investigative
(other than an action by or in the right of the corporation)

                                      II-2



by reason of the fact that he or she is or was a director, officer, employee or
agent of the corporation, or who is or was serving at the request of the
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees), judgments, fines and amounts paid in settlement
actually and reasonably incurred by such person in connection with such action,
suit or proceeding, if such person acted in good faith and in a manner he or she
reasonably believed to be in, or not opposed to the best interests of the
corporation, and, with respect to any criminal action or proceeding, had no
reasonable cause to believe his or her conduct was unlawful. The termination of
any action, suit or proceeding by judgment, order, settlement, conviction, or
upon a plea of nolo contendere or its equivalent, shall not, of itself, create a
presumption that the person did not act in good faith and in a manner which he
or she reasonably believed to be in or not opposed to the best interests of the
corporation or, with respect to any criminal action or proceeding, that the
person had reasonable cause to believe that his or her conduct was unlawful.

         (b)      A corporation may indemnify any person who was or is a party,
or is threatened to be made a party to any threatened, pending or completed
action or suit by or in the right of the corporation to procure a judgment in
its favor by reason of the fact that such person is or was a director, officer,
employee or agent of the corporation, or is or was serving at the request of the
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, against expenses
(including attorneys' fees) actually and reasonably incurred by such person in
connection with the defense or settlement of such action or suit, if such person
acted in good faith and in a manner he or she reasonably believed to be in, or
not opposed to, the best interests of the corporation, provided that no
indemnification shall be made with respect to any claim, issue, or matter as to
which such person has been adjudged to have been liable to the corporation,
unless, and only to the extent that the court in which such action or suit was
brought shall determine upon application that, despite the adjudication of
liability, but in view of all the circumstances of the case, such person is
fairly and reasonably entitled to indemnity for such expenses as the court shall
deem proper.

         (c)      To the extent that a present or former director, officer or
employee of a corporation has been successful, on the merits or otherwise, in
the defense of any action, suit or proceeding referred to in subsections (a) and
(b), or in defense of any claim, issue or matter therein, such person shall be
indemnified against expenses (including attorneys' fees) actually and reasonably
incurred by such person in connection therewith if the person acted in good
faith and in a manner he or she reasonably believed to be in, or not opposed to,
the best interests of the corporation.

         (d)      Any indemnification under subsections (a) and (b) (unless
ordered by a court) shall be made by the corporation only as authorized in the
specific case, upon a determination that indemnification of the present or
former director, officer, employee or agent is proper in the circumstances
because he or she has met the applicable standard of conduct set forth in
subsections (a) or (b). Such determination shall be made with respect to a
person who is a director or officer at the time of the determination: (1) by the
majority vote of the directors who are not parties to such action, suit or
proceeding, even though less than a quorum, (2) by a committee of the directors
designated by a majority vote of the directors, even though less than a quorum,
(3) if there are no such directors, or if the directors so direct, by
independent legal counsel in a written opinion, or (4) by the shareholders.

         (e)      Expenses (including attorney's fees) incurred by an officer or
director in defending a civil or criminal action, suit or proceeding may be paid
by the corporation in advance of the final disposition of such action, suit or
proceeding upon receipt of an undertaking by or on behalf of the director or
officer to repay such amount if it shall ultimately be determined that such
person is not entitled to be indemnified by the corporation as authorized in
this Section. Such expenses (including attorneys' fees) incurred by former
directors and officers or other employees and agents may be so paid on such
terms and conditions, if any, as the corporation deems appropriate.

                                      II-3



         (f)      The indemnification and advancement of expenses provided by or
granted under the other subsections of this Section shall not be deemed
exclusive of any other rights to which those seeking indemnification or
advancement of expenses may be entitled under any by-law, agreement, vote of
shareholders or disinterested directors, or otherwise, both as to action in his
or her official capacity and as to action in another capacity while holding such
office.

         (g)      A corporation may purchase and maintain insurance on behalf of
any person who is or was a director, officer, employee or agent of the
corporation, or who is or was serving at the request of the corporation as a
director, officer, employee or agent of another corporation, partnership, joint
venture, trust or other enterprise, against any liability asserted against such
person and incurred by such person in any such capacity, or arising out of his
or her status as such, whether or not the corporation would have the power to
indemnify such person against such liability under the provisions of this
Section.

         (h)      If a corporation indemnifies or advances expenses to a
director or officer under subsection (b) of this Section, the corporation shall
report the indemnification or advance in writing to the shareholders with or
before the notice of the next shareholders meeting.

         (i)      For purposes of this Section, references to "the corporation"
shall include, in addition to the surviving corporation, any merging corporation
(including any corporation having merged with a merging corporation) absorbed in
a merger which, if its separate existence had continued, would have had the
power and authority to indemnify its directors, officers, and employees or
agents, so that any person who was a director, officer, employee or agent of
such merging corporation, or was serving at the request of such merging
corporation as a director, officer, employee or agent of another corporation,
partnership, joint venture, trust or other enterprise, shall stand in the same
position under the provisions of this Section with respect to the surviving
corporation as such person would have with respect to such merging corporation
if its separate existence had continued.

         (j)      For purposes of this Section, reference to "other enterprises"
shall include employee benefit plans; references to "fines" shall include any
excise taxes assessed on a person with respect to an employee benefit plan; and
references to "serving at the request of the corporation" shall include any
service as a director, officer, employee or agent of the corporation which
imposes duties on, or involves services by such director, officer, employee, or
agent with respect to an employee benefit plan, its participants, or
beneficiaries. A person who acted in good faith and in a manner he or she
reasonably believed to be in the best interests of the participants and
beneficiaries of an employee benefit plan shall be deemed to have acted in a
manner "not opposed to the best interest of the corporation" as referred to in
this Section.

         (k)      The indemnification and advancement of expenses provided by or
granted under this Section shall, unless otherwise provided when authorized or
ratified, continue as to a person who has ceased to be a director, officer,
employee, or agent and shall inure to the benefit of the heirs, executors, and
administrators of that person.

         (l)      The changes to this Section made by this amendatory Act of the
92nd General Assembly apply only to actions commenced on or after the effective
date of this amendatory Act of the 92nd General Assembly. (Last amended by P.A.
92-0033, L. '01, eff. 7-1-01.)

         Wintrust has purchased $30 million of insurance policies which insure
Wintrust's directors and officers against liability which they may incur as a
result of actions taken in such capacities. In addition, Wintrust maintains
fiduciary liability coverage up to a $5 million limit and trust errors and
omissions coverage up to a limit of $15 million.

                                      II-4



ITEM 16.  EXHIBITS

3.1      Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

3.2      Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

3.3      Amended and Restated By-laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q
         for the quarter ended March 31, 2003).

4.1      Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

4.2      Certain instruments defining the rights of holders of long-term debt of
         Wintrust and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         Wintrust and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. Wintrust hereby agrees to furnish a copy of any of
         these agreements to the Commission upon request.

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. regarding legality.*

23.1     Consent of Ernst & Young LLP.*

23.2     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in opinion
         filed as Exhibit 5.1).

24.1     Power of Attorney (set forth on signature page to this Registration
         Statement).


------------------
*       Filed herewith.

ITEM 17.  UNDERTAKINGS

         (a)      We hereby undertake:

                  (1) To file, during any period in which offers or sales are
being made, a post-effective amendment to this registration statement:

                           (i) to include any prospectus required by Section
                  10(a)(3) of the Securities Act of 1933;

                           (ii) to reflect in the prospectus any facts or events
                  arising after the effective date of the registration statement
                  (or the most recent post-effective amendment thereof) which,
                  individually or in the aggregate, represent a fundamental
                  change in the information set forth in the registration
                  statement. Notwithstanding the foregoing, any increase or
                  decrease in volume of securities offered (if the total dollar
                  value of securities offered would not exceed that which was
                  registered) and any deviation from the low or high end of the
                  estimated maximum offering range may be reflected in the form
                  of prospectus filed with the Commission pursuant to Rule
                  424(b) if, in the aggregate, the

                                      II-5



                  changes in volume and price represent no more than a 20
                  percent change in the maximum aggregate offering price set
                  forth in the "Calculation of Registration Fee" table in the
                  effective registration statement; and

                           (iii) to include any material information with
                  respect to the plan of distribution not previously disclosed
                  in the registration statement or any material change to such
                  information in the registration statement;

provided, however, that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if the
information required to be included in a post-effective amendment by those
paragraphs is contained in periodic reports filed with or furnished to the
Commission by the registrant pursuant to Section 13 or 15(d) of the Securities
Exchange Act of 1934 that are incorporated by reference in the registration
statement.

                  (2) That, for the purpose of determining any liability under
the Securities Act of 1933, each such post-effective amendment shall be deemed
to be a new registration statement relating to the securities offered therein,
and the offering of such securities at that time shall be deemed to be the
initial bona fide offering thereof; and

                  (3) To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the
termination of the offering.

         (b)      We hereby undertake that, for purposes of determining any
liability under the Securities Act of 1933, each filing of the registrant's
annual report pursuant to Section 13(a) or Section 15(d) of the Securities
Exchange Act of 1934 that is incorporated by reference in this registration
statement shall be deemed to be a new registration statement relating to the
securities offered herein, and the offering of such securities at that time
shall be deemed to be the initial bona fide offering thereof.

         (c)      Insofar as indemnification for liabilities arising under the
Securities Act of 1933 may be permitted to directors, officers and controlling
persons of the registrant pursuant to the foregoing provisions, or otherwise,
the registrant has been advised that in the opinion of the Securities and
Exchange Commission such indemnification is against public policy as expressed
in the Act and is, therefore, unenforceable. In the event that a claim for
indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit to a court of appropriate jurisdiction the question whether such
indemnification by it is against public policy as expressed in the Act and will
be governed by the final adjudication of such issue.

                                      II-6



                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, as amended,
the registrant certifies that it has reasonable grounds to believe that it meets
all of the requirements for filing on Form S-3 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Lake Forest, State of Illinois, on this 26th day
of May, 2004.

                           WINTRUST FINANCIAL CORPORATION

                           By:    /s/ David A. Dykstra
                              --------------------------------------------------
                              David A. Dykstra
                              Senior Executive Vice President and
                              Chief Operating Officer

         We, the undersigned directors of Wintrust Financial Corporation, and
each of us, do hereby constitute and appoint each and any of Edward J. Wehmer
and David A. Dykstra, our true and lawful attorneys and agents, with full power
of substitution and resubstitution, to do any and all acts and things in our
name and behalf in any and all capacities and to execute any and all instruments
for us in our names in any and all capacities, which attorney and agent may deem
necessary or advisable to enable said corporation to comply with the Securities
Act of 1933, as amended, and any rules, regulations, and requirements of the
Securities and Exchange Commission, in connection with this Registration
Statement, including specifically, but without limitation, power and authority
to sign for us or any of us in our names in the capacities indicated below, any
and all amendments (including post-effective amendments) hereto and any other
registration statements related to the offering that is the subject of this
registration statement filed pursuant to Rule 462; and we do hereby ratify and
confirm all that said attorney and agent, or his substitute, shall do or cause
to be done by virtue thereof.

         Pursuant to the requirements of the Securities Act of 1933, this
Registration Statement has been signed by the following persons on the 26th day
of May, 2004 in the capacities indicated.

             SIGNATURE                              TITLE
             ---------                              -----

/s/  Edward J. Wehmer                      President, Chief Executive
----------------------------------            Officer and Director
     Edward J. Wehmer

/s/  David L. Stoehr                      Executive Vice President and
----------------------------------           Chief Financial Officer
     David L. Stoehr                (Principal Financial and Accounting Officer)

/s/  John S. Lillard                         Chairman and Director
----------------------------------
     John S. Lillard

/s/  Peter D. Crist                                   Director
----------------------------------
     Peter D. Crist

/s/  Bruce K. Crowther                                Director
----------------------------------
     Bruce K. Crowther

/s/  Bert A. Getz, Jr.                                Director
----------------------------------
     Bert A. Getz, Jr.

                                      S-1



             SIGNATURE                              TITLE
             ---------                              -----

/s/  Philip W. Hummer                                 Director
----------------------------------
     Philip W. Hummer

/s/  James B. McCarthy                                Director
----------------------------------
     James B. McCarthy

/s/  Marguerite Savard McKenna
----------------------------------                    Director
     Marguerite Savard McKenna

/s/  Albin F. Moschner                                Director
----------------------------------
     Albin F. Moschner

/s/  Thomas J. Neis                                   Director
----------------------------------
     Thomas J. Neis

/s/  Hollis W. Rademacher                             Director
----------------------------------
     Hollis W. Rademacher

/s/ J. Christopher Reyes                              Director
----------------------------------
    J. Christopher Reyes

/s/ John J. Schornack                                 Director
----------------------------------
    John J. Schornack

/s/  Ingrid S. Stafford                               Director
----------------------------------
     Ingrid S. Stafford

                                      S-2



                                  EXHIBIT INDEX

3.1      Amended and Restated Articles of Incorporation of Wintrust Financial
         Corporation (incorporated by reference to Exhibit 3.1 of the Company's
         Form S-1 Registration Statement (No. 333-18699) filed with the
         Securities and Exchange Commission on December 24, 1996).

3.2      Statement of Resolution Establishing Series of Junior Serial Preferred
         Stock A of Wintrust Financial Corporation (incorporated by reference to
         Exhibit 3.2 of the Company's Form 10-K for the year ended December 31,
         1998).

3.3      Amended and Restated By-laws of Wintrust Financial Corporation
         (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q
         for the quarter ended March 31, 2003).

4.1      Rights Agreement between Wintrust Financial Corporation and Illinois
         Stock Transfer Company, as Rights Agent, dated July 28, 1998
         (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A
         Registration Statement (No. 000-21923) filed with the Securities and
         Exchange Commission on August 28, 1998).

4.2      Certain instruments defining the rights of holders of long-term debt of
         Wintrust and certain of its subsidiaries, none of which authorize a
         total amount of indebtedness in excess of 10% of the total assets of
         Wintrust and its subsidiaries on a consolidated basis, have not been
         filed as Exhibits. Wintrust hereby agrees to furnish a copy of any of
         these agreements to the Commission upon request.

5.1      Opinion of Vedder, Price, Kaufman & Kammholz, P.C. regarding legality.*

23.1     Consent of Ernst & Young LLP.*

23.2     Consent of Vedder, Price, Kaufman & Kammholz, P.C. (included in opinion
         filed as Exhibit 5.1).

24.1     Power of Attorney (set forth on signature page to this Registration
         Statement).


------------------
*       Filed herewith.