Serving today's active sailor, Fairwind Sail Charters is Chicago's oldest American Sailing Association training facility and premier Sailing Yacht Lease Share Program where you can sail your own yacht all season long for a fraction of what it costs to rent or own.  Beautiful yachts, unparalleled personal service, and the best rates anywhere have made Fairwind Sail Charters the choice of Chicagoland sailors for sailing instruction, sailing lease share, and private sailing charters for over three decades.

Haven't you waited long enough?  Getting started in sailing can be a daunting and expensive endeavor, but with Fairwind Sail Charters you get a legacy of friendly, straight-talking folks dedicated to making your sailing dreams a reality.  Since 1978, Fairwind Sail Charters has set the standard for Chicagoland sailing, providing the best in quality, value, and service.