Our first 70+ degree day here in Key Midwest this season! Definitely time to shake off the winter doldrums and start gearing up for sailing season. Whether you are a new sailor looking for sailing lessons or an Old Salt looking for Chicago’s best sailing value, make Fairwind Sail Charters your home port. Chicago’s oldest American Sailing Association sailing school and a fleet of beautiful Beneteau sailing yachts for lease share make Fairwind Sail Charters your one-stop shop for Chicago sailing. We are also taking reservations for our private sailing charters, so if you have a Special Day you would like to celebrate with a Special Someone contact us now for an unforgettable sailing experience.