Company: WTFCN
Filing Date: 2025-04-03
Form Type: DEFA14A
Source: 0001104659-25-031677
Chunk: 0

Company: WINTRUST FINANCIAL CORP
Filing Date: 2025-04-03
Form: DEFA14A
Chunk 0
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<div align='center'>UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, DC 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of
the
Securities Exchange Act of 934</div>

Filed by the Registrant x

Filed by a Party other than the Registrant ¨

Check the appropriate box:

| ¨ | Preliminary Proxy Statement                                                     |
| ¨ | Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |
| ¨ | Definitive Proxy Statement                                                      |
| x | Definitive Additional Materials                                                 |
| ¨ | Soliciting Material under § 240.14a-12                                          |

<div align='center'>Wintrust Financial Corporation

(Name of Registrant as Specified in its Charter)

(Name of Person(s) Filing Proxy Statement,
if Other Than the Registrant)</div>

Payment of Filing Fee (Check all boxes that apply):

| x | No fee required.                                                                                    |
| ¨ | Fee paid previously with preliminary materials.                                                     |
| ¨ | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11 |

| 1. Election of Directors                                                                                                              
 Elizabeth H. Connelly                                                                                                                 
 Timothy S. Crane                                                                                                                      
 Peter D. Crist                                                                                                                        
 William J. Doyle                                                                                                                      
 Marla F. Glabe                                                                                                                        
 H. Patrick Hackett, Jr.                                                                                                               
 Brian A. Kenney                                                                                                                       
 Deborah L. Hall Lefevre                                                                                                               
 Suzet M. McKinney                                                                                                                     
 Richard L. Postma                                                                                                                     
 Gregory A. Smith                                                                                                                      
 Karin Gustafson Teglia                                                                                                                
 Alex E. Washington, III                                                                                                               
 Important Notice Regarding the Availability of Proxy Materials for the Annual Shareholder Meeting of                                  
 WINTRUST FINANCIAL CORPORATION                                                                                                        
 To Be Held On:                                                                                                                        
 May 22, 2025 at 9:00 a.m. (Central Time)                                                                                              
 at 9700 West Higgins Road, 2nd Floor, Rosemont, Illinois 60018                                                                        
 This communication presents only an overview of the more complete proxy materials that are available to you on the Internet. We       
 encourage you to access and review all of the important information contained in the proxy materials before voting.                   
 If you want to receive