Sailapalooza Presented by Wintrust

by Annie Thompson

August 6, 2026

The boats went out in the morning, sails up against the downtown skyline, as half of the thirty-five girls from Girls in the Game learned to steer, trim, and read the wind on Lake Michigan. The other half were a few steps away in the pool, having swim lessons. After lunch, they traded places. Sail and swim, same day, same place.

The combination of sailing and swimming lessons made this year's Sailapalooza, presented by Wintrust, so special. In its second year, the event moved to a new home on the South Side: 31st Street Harbor, the only CYCF site where a harbor and a pool sit side by side. Girls in the Game runs year-round sports and health programming for girls across Chicago, and Sailapalooza fits naturally into what they already do.

Lake Michigan belongs to every kid in this city, but real time on the water is hard to come by, even when it is only minutes from home. Over four days in July, the girls turned their fear into joy on the water and in the pool. One camper was nervous to wade in the pool on Monday. By Thursday afternoon, she belly laughed while playing Marco Polo in the pool with her friends.  

On three J/100s, a Merit 25, and an Olson 25, most of the girls were sailing for the first time, and some took the tiller themselves. "It was my first time ever driving a sailboat!" said Kayla B. "It was cool but a little tricky with everything going opposite."

Sailapalooza, presented by Wintrust, is part of Wintrust's longstanding commitment to strengthening the communities where its people live and work. That support extends beyond sponsorship: Ian Burns, a Wintrust vice president and assistant general counsel, joined the Chicago Yacht Club Foundation board as secretary this year.

"One of the things I enjoy most about Sailapalooza is seeing kids discover what they're capable of. For many of them, it's their first time on the water, and by the end of the week, you can see their confidence grow. Wintrust is proud to partner with the Chicago Yacht Club Foundation to help create those opportunities," said Burns.

For most of these girls, the whole scene—the boats, the pool, the skyline from the water—was brand-new.