Wolcott’s Annual Benefit is more than just a night of celebration—it’s one of the most impactful events of the year. Parents, alumni, faculty, staff, and friends come together for an evening of joy and philanthropy, with one shared purpose: to support scholarships for Wolcott students.

A Yacht Rock Evening | Anchored in Excellence

Join us on Thursday, April 15, 2027, for the Annual Spring Benefit Dinner & Auction at the Wolcott Arts & Athletics Center, 1950 W Hubbard Street. The evening includes dinner, a live band playing the smooth hits of the ’70s and ’80s, a live auction, and performances by Wolcott students. Nautical chic is the attire! Come dress in in yacht wear, boat shoes, captain hats, and other fun attire! 

All proceeds support the school’s greatest needs, including tuition assistance. 

Donate an Auction Item
The auction depends on items from our families and friends. Gift certificates, experiences, vacation stays, and event tickets are all welcome. If you or your business would like to contribute, please complete the Auction Items Donation Form. 

Become a Sponsor
Sponsorships start at $1,000. Depending on the level, benefits include event tickets, recognition in the program book and on the school website, and dedicated event signage. Sponsors committed by Monday, March 29, 2027, will be listed in the program book and event materials. [Sponsorship link coming soon!]

Questions? Contact Kelly Ramos, Director of Development, at 312.610.4927 or kramos@wolcottschool.org.