As filed with the Securities and Exchange Commission on December ___, 2000
                                                           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 LAKE
                           LAKE FOREST, ILLINOIS 60045
    (Address, including zip code of registrant's principal executive office)
                              --------------------

                         WINTRUST FINANCIAL CORPORATION
                            RETIREMENT SAVINGS 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



===================================================================================================================================
                                                     Proposed Maximum
   Title of Securities             Amount to             Offering             Proposed Maximum              Amount of
     be Registered               be Registered       Price Per Share      Aggregate Offering Price      Registration Fee
- ----------------------------     --------------      -----------------    -----------------------       -----------------
                                                                                             

Common Stock, without par          100,000             $15.6875(3)         $1,568,750                    $393
value (1) (2)
===================================================================================================================================
(1)       Reflects shares that may be issued pursuant to the Wintrust Financial
          Corporation Retirement Savings Plan.

(2)       In addition, pursuant to Rule 416(c), this registration statement also
          covers an indeterminate amount of interests to be offered or sold
          pursuant to the Wintrust Financial Corporation Retirement Savings Plan
          described herein.

(3)       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 December 21, 2000.

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




                                     PART I

                    INFORMATION REQUIRED IN THE SECTION 10(a)

                                   PROSPECTUS

Note:     Documents containing the information required by this section will be
          given to employees eligible to participate in the Wintrust Financial
          Corporation Retirement Savings Plan (the "Plan"), and are not required
          to be filed with the Commission as a part of the
          Registration Statement.


                                        1




                                     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 dates, in this Registration Statement
by reference:


     A.   Wintrust's Annual Report on Form 10-K for the fiscal year ended
          December 31, 1999.

     B. Wintrust's Quarterly Report on Form 10-Q for the period ended March 31,
2000.

     C. Wintrust's Quarterly Report on Form 10-Q for the period ended June 30,
2000.

     D.   Wintrust's Quarterly Report on Form 10-Q for the period ended
          September 30, 2000.

     E.   Current Reports on Form 8-K dated January 24, 2000, January 27, 2000
          and September 7, 2000.

     F.   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) on January 3, 1997 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 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.

                                        2



          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.

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

                                        3


          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 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.

                                        4



     (h)  If a corporation has paid indemnity or has advanced expenses to a
director, officer, employee or agent, 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. 88-43, L. '93, eff. 1-1-94.)

     Wintrust has purchased $20 million in insurance policies which insures
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.

     Reference is made to the Exhibit Index which is incorporated herein by
reference. The undersigned registrant hereby undertakes that it will submit the
Wintrust Financial Corporation Retirement Savings Plan and any amendments
thereto to the Internal Revenue Service, and has made or will make all changes
required by the IRS in order to qualify the plan.

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.

                                        5



               (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.

          (h)  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 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 21st day of
December, 2000.

                                          Wintrust Financial Corporation



                                          By:  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 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 21st day
of December, 2000 in the capacities indicated.


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


          EDWARD J. WEHMER                President and Chief Executive Officer
- -------------------------------------                   and Director
          Edward J. Wehmer


          DAVID A. DYKSTRA                       Executive Vice President
- -------------------------------------           and Chief Financial Officer
          David A. Dykstra                     (Principal Financial Officer)


          JOHN S. LILLARD                           Chairman and Director
- ------------------------------------
          John S. Lillard


          JOSEPH ALAIMO                                   Director
- ------------------------------------
          Joseph Alaimo


          PETER CRIST                                     Director
- ------------------------------------
          Peter Crist

                                        7



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


- ------------------------------------                      Director
          Bruce K. Crowther


         MAURICE F. DUNNE, JR.                            Director
- ------------------------------------
         Maurice F. Dunne, Jr.


         WILLIAM C. GRAFT                                 Director
- ------------------------------------
         William C. Graft


         KATHLEEN R. HORNE                                Director
- ------------------------------------
         Kathleen R. Horne


         JOHN W. LEOPOLD                                  Director
- ------------------------------------
         John W. Leopold


                                                          Director
- ------------------------------------
        James E. Mahoney


        JAMES B. McCARTHY                                 Director
- ------------------------------------
        James B. McCarthy


        MARGUERITE SAVARD McKENNA                         Director
- ------------------------------------
        Marguerite Savard McKenna


                                                          Director
- ------------------------------------
        Albin F. Moschner


        DOROTHY M. MUELLER                                Director
- ------------------------------------
        Dorothy M. Meuller



        THOMAS J. NEIS                                    Director
- ------------------------------------
        Thomas J. Neis


                                        8



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


        HOLLIS W. RADEMACHER                              Director
- ------------------------------------
        Hollis W. Rademacher


                                                          Director
- ------------------------------------
        J.Christopher Reyes


- ------------------------------------                      Director
        Peter Rusin


        JOHN N. SCHAPER                                   Director
- ------------------------------------
        John N. Schaper


                                                          Director
- ------------------------------------
        John J. Schornack


        INGRID S. STAFFORD                                Director
- ------------------------------------
        Ingrid S. Stafford


        JANE R. STEIN                                     Director
- ------------------------------------
        Jane R. Stein


        KATHARINE V. SYLVESTER                            Director
- ------------------------------------
        Katharine V. Sylvester


                                                          Director
- ------------------------------------
        Larry Wright


                                        9



     Pursuant to the requirements of the Securities Act of 1933, the trustee,
Wintrust Asset Management Company, 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 December 21, 2000.


                          Wintrust Financial Corporation Retirement Savings Plan



                          By:  ANITA E. MORRIS
                               -------------------------------------------------
                               Anita E. Morris
                               Vice President
                               Wintrust Asset Management Company

                                       10





                                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 the Company's Form 10-Q for the quarter
          ended June 30, 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.

23.2      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).


                                       11