Windy City Sailing, Inc.

Windy City Sailing offers luxury sailboat charters for groups of 1 to 10 people. Their yachts are equipped with up-to-date amenities and two bathrooms, and they provide customized Chicago sailing cruises with captains and crew. They also offer bareboat charters and special event yacht charters for holidays like the 4th of July and the Chicago Air and Water Show.

Charter extensions are available, and guests are encouraged to bring food and refreshments. Safety is a top priority, with professionally maintained yachts and USCG-certified captains. The yachts are located at the North End of Belmont Harbor, just east of Wrigley Field, and are easily accessible via Uber, Lyft, taxis, and bicycles.