EXHIBIT 5.1


                                                May 25, 2001


Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois  60045

         Re:      Registration Statement on Form S-8

Gentlemen:

     We are acting as counsel to Wintrust Financial Corporation (the "Company")
in connection with the filing with the Securities and Exchange Commission of a
Registration Statement on Form S-8 (the "Registration Statement") relating to up
to 150,000 shares of the Company's common stock, without par value (the "Common
Stock"). The Common Stock is issuable under the Wintrust Financial Corporation
Directors Deferred Fee and Stock Plan (the "Plan").

     In connection with our opinion, we have examined originals, or copies,
certified or otherwise identified to our satisfaction, of the Registration
Statement, the Amended and Restated Articles of Incorporation and the Amended
By-Laws of the Company and the Wintrust Financial Corporation Directors Deferred
Fee and Stock Plan, as well as such other corporate records, documents and other
papers as we deemed necessary to examine for purposes of this opinion. We have
assumed the authenticity, accuracy and completeness of all documents submitted
to us as originals, the conformity to authentic original documents of all
documents submitted to us as certified, conformed or photostatic copies and the
genuineness of all signatures.

     Based on the foregoing, we are of the opinion that the shares of Common
Stock when issued by the Company in accordance with the Plan will be duly
authorized, validly issued, fully paid and nonassessable shares of Common Stock.

     The opinion expressed herein is limited to the Federal securities laws and
the laws of the State of Illinois currently in effect.

     We hereby consent to the use of this opinion in connection with the
Registration Statement and to references to our firm therein.

                                        Sincerely yours,



                                        VEDDER, PRICE, KAUFMAN & KAMMHOLZ

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