EXHIBIT 5.1

VEDDER PRICE                           VEDDER, PRICE, KAUFMAN & KAMMHOLZ
                                       222 NORTH LASALLE STREET
                                       CHICAGO, ILLINOIS 60601-1003
                                       312-609-7500
                                       FACSIMILE: 312-609-5005

                                       A PARTNERSHIP INCLUDING VEDDER, PRICE,
                                       KAUFMAN & KAMMHOLZ, P.C.

                                       WITH OFFICES IN CHICAGO AND NEW YORK CITY

                                       March 12, 2002


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

         Re:      Registration Statement on Form S-3
                  ----------------------------------

Gentlemen:

         We are acting as special counsel to Wintrust Financial Corporation, an
Illinois corporation (the "Company"), in connection with the filing with the
Securities and Exchange Commission of a Registration Statement on Form S-3 (the
"Registration Statement") relating to up to 608,495 shares of the Company's
common stock, without par value (the "Common Stock").

         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 By-Laws of
the Company, 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 608,495 shares
of Common Stock that may be offered and sold by selling shareholders pursuant to
and in accordance with the Registration Statement have been duly authorized and
validly issued by the Company and are 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 filing of this opinion as an exhibit to the
Registration Statement and to the use of our name under the heading "Legal
Matters" in the Prospectus included therein.

                                       Very truly yours,


                                       /s/ VEDDER, PRICE, KAUFMAN & KAMMHOLZ