Set against the iconic Chicago waterfront, the Windy City Boat & Yacht Show brings the boating lifestyle to life with immersive experiences for every level of enthusiast. From educational seminars and on-the-water training to elevated social spaces and community-driven moments, this inaugural event goes beyond the docks to celebrate everything that makes boating in the Great Lakes unforgettable. Whether you're stepping aboard for the first time or a seasoned captain, explore the highlights that make this show a must-attend this summer.
Cruisers Classroom
Presented by the Annapolis School of Seamanship
Join us in the Cruisers Classroom presented by the Annapolis School of Seamanship (ASOS) to enhance your boating knowledge and skills with discussions and panels during the show. Covering topics like navigation, docking, maintenance, safety, cruising lifestyle, etc. These sessions run all three days and are perfect for all skill levels and are complimentary for attendees. Seating is limited to 30 per class, no registration required.
On-the-Water Sail Training Classes
Sail America has partnered with SailTime to offer First Sail, an on-the-water sailing class, during the show. Perfect for those seeking a confidence boost or completely new to boating, these 2.5 hour sessions are led by a certified captain and cover essential boating skills from start to finish. Sessions will be in a small group of no more than six people. The classes will be available all three days of the show and are on the show grounds. Pricing is $89 per person and included same-day admission. Registration in advance required as limited spots are available.
Yacht Club Lounge
Inspired by Chicago’s prestigious yacht club tradition, the Yacht Club Lounge offers an elevated waterfront experience during the Windy City Boat & Yacht Show. This inviting space brings together yacht club members and boating enthusiasts in a refined setting designed for connection and conversation. Celebrate Chicago’s rich boating heritage while enjoying the excitement of the show. Special thanks to our anchors; Chicago Yacht Club, Columbia Yacht Club, Burnham Yacht Club and Chicago Harbors for joining us in this lounge.
Anchored in Hope: A Community Sunday
Join us on Sunday, June 14th for a meaningful day on the waterfront dedicated to family, community, and giving back. Anchored in Hope brings together our local charity partners and boating community to celebrate connection, impact, and shared purpose—set against the backdrop of the water in true boating spirit. Enjoy a day of celebration and togetherness as we highlight the organizations making a difference right here in our community.
COMMUNITY PARTNERS
The Windy City Boat & Yacht Show is proud to recognize the outstanding partners who helped make this debut Chicago event possible. We are grateful to the local community, the boating industry, and everyone who supported the launch of this inaugural show. Your enthusiasm and partnership brought this vision to life on the waterfront.
Special thanks to our partners—Chicago Harbors, Suntex Marinas, Choose Chicago, and the Chicago Park District—for their collaboration and commitment in helping establish a new Chicago boating tradition.
