As filed with the Securities and Exchange Commission on May 25, 2001
                                        Registration No. 333-
================================================================================
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

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


                                    FORM S-8
                             REGISTRATION STATEMENT
                                      Under
                           THE SECURITIES ACT OF 1933

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

                         WINTRUST FINANCIAL CORPORATION
             (Exact name of registrant as specified in its charter)


           ILLINOIS                                           36-3873352
  (State or Other Jurisdiction                             (I.R.S. Employer
of Incorporation or Organization)                         Identification No.)

                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
    (Address, including zip code of registrant's principal executive office)

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


                         WINTRUST FINANCIAL CORPORATION
                      DIRECTORS DEFERRED FEE AND STOCK PLAN
                            (Full title of the plan)

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


                                DAVID A. DYKSTRA
                         WINTRUST FINANCIAL CORPORATION
                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
                                 (847) 615-4096
 (Name, address and telephone number, including area code, of agent for service)

                                   Copies To:

                             JENNIFER R. EVANS, ESQ.
                             MARY C. WAGHORNE, ESQ.
                        VEDDER, PRICE, KAUFMAN & KAMMHOLZ
                            222 NORTH LASALLE STREET
                                   SUITE 2500
                             CHICAGO, ILLINOIS 60601
                                 (312) 609-7500

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


                         CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>

===============================================================================================================================
  TITLE OF SECURITIES       AMOUNT TO BE          PROPOSED MAXIMUM               PROPOSED MAXIMUM               AMOUNT OF
   TO BE REGISTERED          REGISTERED      OFFERING PRICE PER SHARE(1)    AGGREGATE OFFERING PRICE(1)      REGISTRATION FEE
-------------------------------------------------------------------------------------------------------------------------------
<S>                          <C>                       <C>                         <C>                        <C>
Common Stock,
without par value*           150,000                   $23.605                     $3,540,750                 $885
===============================================================================================================================
</TABLE>
________________
* Including the preferred share purchase rights associated therewith.
(1)  Estimated solely for the purpose of calculating the registration fee
     pursuant to Rule 457(h)(l) based on the average of the high and low sales
     prices for the Common Stock reported on the Nasdaq National Market on
     May 18, 2001.

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

<PAGE>

                                     PART I

                    INFORMATION REQUIRED IN THE SECTION 10(a)

                                  PROSPECTUSES

Note:    The documents containing the information required by this section will
         be given to those persons who participate in the Wintrust Financial
         Corporation Directors Deferred Fee and Stock Plan, all of whom are
         directors of Wintrust Financial Corporation or its subsidiaries who are
         entitled to Board compensation. Such documents are not required to be
         filed with the Commission as a part of this Registration Statement or
         as an Exhibit.

<PAGE>

                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT


ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

     The following documents filed with the Securities and Exchange Commission
by Wintrust Financial Corporation, an Illinois corporation, are incorporated, as
of their respective filing dates, in this Registration Statement by reference:

     A.   Wintrust's Annual Report on Form 10-K for the fiscal year ended
          December 31, 2000.

     B.   Wintrust's Quarterly Report on Form 10-Q for the quarter ended March
          31, 2001.

     C.   Current Reports on Form 8-K dated February 14, 2001 and May 16, 2001.

     D.   The description of Wintrust's Common Stock contained in Wintrust's
          Registration Statement filed with the Commission pursuant to Section
          12 of the Securities Exchange Act of 1934 on Form 8-A (Registration
          No. 0-21923) filed with the Commission on January 3, 1997 and all
          amendments or reports filed for the purpose of updating such
          description.

     E.   The description of Wintrust's Rights contained in Wintrust's
          Registration Statement filed with the Commission pursuant to Section
          12 of The Securities Exchange Act of 1934 on Form 8-A (Registration
          No. 000-21923) filed with the Commission on August 28, 1998 and all
          amendments or reports filed for the purpose of updating such
          description.

     All documents filed by Wintrust pursuant to Section 13(a), 13(c), 14 and
15(d) of the Securities Exchange Act of 1934 prior to the filing of a
post-effective amendment which indicates that all securities offered have been
sold or which deregisters all securities then remaining unsold are incorporated
by reference in this Registration Statement and are a part hereof from the date
of filing such documents. Any statement contained in a document incorporated or
deemed to be incorporated by reference herein shall be deemed to be modified or
superseded for purposes of this Registration Statement to the extent that a
statement contained herein or in any other subsequently filed document which
also is or is deemed to be incorporated by reference herein modifies or
supersedes such statement. Any such statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of this
Registration Statement.

ITEM 4.  DESCRIPTION OF SECURITIES.

         Not applicable.

ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL.

     The validity of the issuance of the Common Stock offered hereby will be
passed upon for Wintrust by Vedder, Price, Kaufman & Kammholz, Chicago,
Illinois. Douglas J. Lipke, a partner in the law firm of Vedder, Price, Kaufman
& Kammholz, serves as a non-voting advisor to the board of directors of Hinsdale
Bank and Trust Company, a subsidiary of Wintrust.

ITEM 6.  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 Articles 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

                                        2

<PAGE>

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 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.

                                        3

<PAGE>

     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) 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 director, officer, employee or agent 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.

     (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 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 (1) by the Board of Directors by a majority vote of a quorum
consisting of directors who were not parties to such action, suit or proceeding,
or (2) if such a quorum is not obtainable, or, even if obtainable, if a quorum
of disinterested directors so directs, by independent legal counsel in a written
opinion, or (3) by the shareholders.

     (e) Expenses incurred 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, officer, employee or agent to repay such amount if it shall
ultimately be determined that he or she is not entitled to be indemnified by the
corporation as authorized in this Section.

     (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

                                        4

<PAGE>

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. (Last amended by P.A. 91-464, L. '99, eff. 1-1-00.)

     The Company has purchased $20 million in 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 $2 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED.

         Not applicable.

ITEM 8.  EXHIBITS.

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

          4.2  Amended By-Laws of Wintrust Financial Corporation (incorporated
               by reference to Exhibit 3(i) of Wintrust's Form 10-Q for the
               quarter ended June 30, 1998).

          4.3  Wintrust Financial Corporation Directors Deferred Fee and Stock
               Plan (incorporated by reference to Appendix B to Registrant's
               Proxy Statement filed with the Commission on April 27, 2001).

          4.4  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).

                                        5

<PAGE>


          5.1  Opinion of Vedder, Price, Kaufman & Kammholz regarding the
               legality of any original issuance of Common Stock.

          23.1 Consent of Ernst & Young LLP.

          23.2 Consent of KPMG LLP.

          23.3 Consent of Vedder, Price, Kaufman & Kammholz (included in Exhibit
               5.1).

          24.1 Power of Attorney (included on the signature pages of the
               Registration Statement).

ITEM 9.  UNDERTAKINGS.

     (a)  The undersigned registrant hereby undertakes:

          (1)  To file, during any period in which offers or sales are being
               made, a post-effective amendment to this Registration Statement
               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 set forth 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.

          (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)  The undersigned registrant hereby undertakes 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 (and each filing
          of the Plan's annual report pursuant to 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.

                                        6

<PAGE>

                                   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
the requirements for filing on Form S-8 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 25th day of
May, 2001.

                                  Wintrust Financial Corporation


                                  By:  /s/ Edward J. Wehmer
                                           -------------------------------------
                                           Edward J. Wehmer
                                           President and Chief Executive Officer

     We, the undersigned directors of Wintrust Financial Corporation, and each
of us, do hereby constitute and appoint each and any of John S. Lillard, Edward
J. Wehmer and David A. Dykstra our true and lawful attorney and agent, 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 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 25th day
of May, 2001, in the capacities indicated.


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

/s/ Edward J. Wehmer                             President and Chief Executive
-----------------------------------                   Officer and Director
         Edward J. Wehmer
                                                    Executive Vice President
/s/ David A. Dykstra                              and Chief Financial Officer
-----------------------------------              (Principal Financial Officer)
         David A. Dykstra

/s/ Barbara A. Kilian                           Senior Vice President - Finance
-----------------------------------              (Principal Accounting Officer)
         Barbara A. Kilian

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

/s/ Joseph Alaimo                                          Director
-----------------------------------
         Joseph Alaimo

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

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

<PAGE>

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

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

/s/ William C. Graft                                       Director
-----------------------------------
         William C. Graft

/s/ Kathleen R. Horne                                      Director
-----------------------------------
         Kathleen R. Horne

/s/ John W. Leopold                                        Director
-----------------------------------
         John W. Leopold

/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/ Dorothy M. Mueller                                     Director
-----------------------------------
         Dorothy M. Mueller

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

/s/ Christopher J. Perry                                   Director
-----------------------------------
       Christopher J. Perry

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

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

/s/ Peter P. Rusin                                         Director
-----------------------------------
         Peter P. Rusin

/s/ John N. Schaper                                        Director
-----------------------------------
         John N. Schaper

<PAGE>

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

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

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

/s/ Katharine V. Sylvester                                 Director
-----------------------------------
         Katharine V. Sylvester

/s/ Larry V. Wright                                        Director
-----------------------------------
         Larry V. Wright

<PAGE>

                                INDEX TO EXHIBITS



EXHIBIT
NUMBER                      DESCRIPTION OF EXHIBIT
------                      ----------------------

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

4.2  Amended By-Laws of Wintrust Financial Corporation (incorporated by
     reference to Exhibit 3(i) of Wintrust's Form 10-Q for the quarter ended
     June 30, 1998).

4.3  Wintrust Financial Corporation Directors Deferred Fee and Stock Plan
     (incorporated by reference to Appendix B to Registrant's Proxy Statement
     filed with the Commission on April 27, 2001).

4.4  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).

5.1  Opinion of Vedder, Price, Kaufman & Kammholz regarding the legality of any
     original issuance of Common Stock.

23.1 Consent of Ernst & Young, LLP.

23.2 Consent of KPMG LLP.

23.3 Consent of Vedder, Price, Kaufman & Kammholz (included in Exhibit 5.1).

24.1 Power of Attorney (included on the signature pages of the Registration
     Statement).

                                       10

<PAGE>

                                   EXHIBIT 5.1


                  OPINION OF VEDDER, PRICE, KAUFMAN & KAMMHOLZ




                                                        11
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As filed with the Securities and Exchange Commission on May 25, 2001
                                        Registration No. 333-
================================================================================
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

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

                                    FORM S-8
                             REGISTRATION STATEMENT
                                      Under
                           THE SECURITIES ACT OF 1933

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

                         WINTRUST FINANCIAL CORPORATION
             (Exact name of registrant as specified in its charter)

           ILLINOIS                                           36-3873352
  (State or Other Jurisdiction                             (I.R.S. Employer
of Incorporation or Organization)                         Identification No.)

                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
    (Address, including zip code of registrant's principal executive office)

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

                         WINTRUST FINANCIAL CORPORATION
                      DIRECTORS DEFERRED FEE AND STOCK PLAN
                            (Full title of the plan)

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

                                DAVID A. DYKSTRA
                         WINTRUST FINANCIAL CORPORATION
                               727 NORTH BANK LANE
                           LAKE FOREST, ILLINOIS 60045
                                 (847) 615-4096
 (Name, address and telephone number, including area code, of agent for service)

                                   Copies To:

                             JENNIFER R. EVANS, ESQ.
                             MARY C. WAGHORNE, ESQ.
                        VEDDER, PRICE, KAUFMAN & KAMMHOLZ
                            222 NORTH LASALLE STREET
                                   SUITE 2500
                             CHICAGO, ILLINOIS 60601
                                 (312) 609-7500

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

                         CALCULATION OF REGISTRATION FEE
===============================================================================================================================
  TITLE OF SECURITIES       AMOUNT TO BE          PROPOSED MAXIMUM               PROPOSED MAXIMUM               AMOUNT OF
   TO BE REGISTERED          REGISTERED      OFFERING PRICE PER SHARE(1)    AGGREGATE OFFERING PRICE(1)      REGISTRATION FEE
-------------------------------------------------------------------------------------------------------------------------------
Common Stock,
without par value*           150,000                   $23.605                     $3,540,750                 $885
===============================================================================================================================
________________
* Including the preferred share purchase rights associated therewith.
(1)  Estimated solely for the purpose of calculating the registration fee
     pursuant to Rule 457(h)(l) based on the average of the high and low sales
     prices for the Common Stock reported on the Nasdaq National Market on
     May 18, 2001.

================================================================================
PART I

                    INFORMATION REQUIRED IN THE SECTION 10(a)

                                  PROSPECTUSES

Note:    The documents containing the information required by this section will
         be given to those persons who participate in the Wintrust Financial
         Corporation Directors Deferred Fee and Stock Plan, all of whom are
         directors of Wintrust Financial Corporation or its subsidiaries who are
         entitled to Board compensation. Such documents are not required to be
         filed with the Commission as a part of this Registration Statement or
         as an Exhibit.
PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

     The following documents filed with the Securities and Exchange Commission
by Wintrust Financial Corporation, an Illinois corporation, are incorporated, as
of their respective filing dates, in this Registration Statement by reference:

     A.   Wintrust's Annual Report on Form 10-K for the fiscal year ended
          December 31, 2000.

     B.   Wintrust's Quarterly Report on Form 10-Q for the quarter ended March
          31, 2001.

     C.   Current Reports on Form 8-K dated February 14, 2001 and May 16, 2001.

     D.   The description of Wintrust's Common Stock contained in Wintrust's
          Registration Statement filed with the Commission pursuant to Section
          12 of the Securities Exchange Act of 1934 on Form 8-A (Registration
          No. 0-21923) filed with the Commission on January 3, 1997 and all
          amendments or reports filed for the purpose of updating such
          description.

     E.   The description of Wintrust's Rights contained in Wintrust's
          Registration Statement filed with the Commission pursuant to Section
          12 of The Securities Exchange Act of 1934 on Form 8-A (Registration
          No. 000-21923) filed with the Commission on August 28, 1998 and all
          amendments or reports filed for the purpose of updating such
          description.

     All documents filed by Wintrust pursuant to Section 13(a), 13(c), 14 and
15(d) of the Securities Exchange Act of 1934 prior to the filing of a
post-effective amendment which indicates that all securities offered have been
sold or which deregisters all securities then remaining unsold are incorporated
by reference in this Registration Statement and are a part hereof from the date
of filing such documents. Any statement contained in a document incorporated or
deemed to be incorporated by reference herein shall be deemed to be modified or
superseded for purposes of this Registration Statement to the extent that a
statement contained herein or in any other subsequently filed document which
also is or is deemed to be incorporated by reference herein modifies or
supersedes such statement. Any such statement so modified or superseded shall
not be deemed, except as so modified or superseded, to constitute a part of this
Registration Statement.

ITEM 4.  DESCRIPTION OF SECURITIES.

         Not applicable.

ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL.

     The validity of the issuance of the Common Stock offered hereby will be
passed upon for Wintrust by Vedder, Price, Kaufman & Kammholz, Chicago,
Illinois. Douglas J. Lipke, a partner in the law firm of Vedder, Price, Kaufman
& Kammholz, serves as a non-voting advisor to the board of directors of Hinsdale
Bank and Trust Company, a subsidiary of Wintrust.

ITEM 6.  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 Articles 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

                                        2
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 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.

                                        3
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) 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 director, officer, employee or agent 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.

     (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 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 (1) by the Board of Directors by a majority vote of a quorum
consisting of directors who were not parties to such action, suit or proceeding,
or (2) if such a quorum is not obtainable, or, even if obtainable, if a quorum
of disinterested directors so directs, by independent legal counsel in a written
opinion, or (3) by the shareholders.

     (e) Expenses incurred 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, officer, employee or agent to repay such amount if it shall
ultimately be determined that he or she is not entitled to be indemnified by the
corporation as authorized in this Section.

     (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

                                        4
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. (Last amended by P.A. 91-464, L. '99, eff. 1-1-00.)

     The Company has purchased $20 million in 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 $2 million limit and trust errors and
omissions coverage up to a limit of $15 million.

ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED.

         Not applicable.

ITEM 8.  EXHIBITS.

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

          4.2  Amended By-Laws of Wintrust Financial Corporation (incorporated
               by reference to Exhibit 3(i) of Wintrust's Form 10-Q for the
               quarter ended June 30, 1998).

          4.3  Wintrust Financial Corporation Directors Deferred Fee and Stock
               Plan (incorporated by reference to Appendix B to Registrant's
               Proxy Statement filed with the Commission on April 27, 2001).

          4.4  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).

                                        5
5.1  Opinion of Vedder, Price, Kaufman & Kammholz regarding the
               legality of any original issuance of Common Stock.

          23.1 Consent of Ernst & Young LLP.

          23.2 Consent of KPMG LLP.

          23.3 Consent of Vedder, Price, Kaufman & Kammholz (included in Exhibit
               5.1).

          24.1 Power of Attorney (included on the signature pages of the
               Registration Statement).

ITEM 9.  UNDERTAKINGS.

     (a)  The undersigned registrant hereby undertakes:

          (1)  To file, during any period in which offers or sales are being
               made, a post-effective amendment to this Registration Statement
               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 set forth 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.

          (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)  The undersigned registrant hereby undertakes 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 (and each filing
          of the Plan's annual report pursuant to 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.

                                        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
the requirements for filing on Form S-8 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 25th day of
May, 2001.

                                  Wintrust Financial Corporation

                                  By:  /s/ Edward J. Wehmer
                                           -------------------------------------
                                           Edward J. Wehmer
                                           President and Chief Executive Officer

     We, the undersigned directors of Wintrust Financial Corporation, and each
of us, do hereby constitute and appoint each and any of John S. Lillard, Edward
J. Wehmer and David A. Dykstra our true and lawful attorney and agent, 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 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 25th day
of May, 2001, in the capacities indicated.

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

/s/ Edward J. Wehmer                             President and Chief Executive
-----------------------------------                   Officer and Director
         Edward J. Wehmer
                                                    Executive Vice President
/s/ David A. Dykstra                              and Chief Financial Officer
-----------------------------------              (Principal Financial Officer)
         David A. Dykstra

/s/ Barbara A. Kilian                           Senior Vice President - Finance
-----------------------------------              (Principal Accounting Officer)
         Barbara A. Kilian

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

/s/ Joseph Alaimo                                          Director
-----------------------------------
         Joseph Alaimo

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

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

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

/s/ William C. Graft                                       Director
-----------------------------------
         William C. Graft

/s/ Kathleen R. Horne                                      Director
-----------------------------------
         Kathleen R. Horne

/s/ John W. Leopold                                        Director
-----------------------------------
         John W. Leopold

/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/ Dorothy M. Mueller                                     Director
-----------------------------------
         Dorothy M. Mueller

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

/s/ Christopher J. Perry                                   Director
-----------------------------------
       Christopher J. Perry

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

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

/s/ Peter P. Rusin                                         Director
-----------------------------------
         Peter P. Rusin

/s/ John N. Schaper                                        Director
-----------------------------------
         John N. Schaper
SIGNATURE                                      TITLE
             ---------                                      -----

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

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

/s/ Katharine V. Sylvester                                 Director
-----------------------------------
         Katharine V. Sylvester

/s/ Larry V. Wright                                        Director
-----------------------------------
         Larry V. Wright
INDEX TO EXHIBITS

EXHIBIT
NUMBER                      DESCRIPTION OF EXHIBIT
------                      ----------------------

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

4.2  Amended By-Laws of Wintrust Financial Corporation (incorporated by
     reference to Exhibit 3(i) of Wintrust's Form 10-Q for the quarter ended
     June 30, 1998).

4.3  Wintrust Financial Corporation Directors Deferred Fee and Stock Plan
     (incorporated by reference to Appendix B to Registrant's Proxy Statement
     filed with the Commission on April 27, 2001).

4.4  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).

5.1  Opinion of Vedder, Price, Kaufman & Kammholz regarding the legality of any
     original issuance of Common Stock.

23.1 Consent of Ernst & Young, LLP.

23.2 Consent of KPMG LLP.

23.3 Consent of Vedder, Price, Kaufman & Kammholz (included in Exhibit 5.1).

24.1 Power of Attorney (included on the signature pages of the Registration
     Statement).

                                       10
EXHIBIT 5.1

                  OPINION OF VEDDER, PRICE, KAUFMAN & KAMMHOLZ

                                                        11