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Chicago’s Sailing Standard Since 1978

Celebrating 36 Years of Service!

Serving today’s active sailor, Fairwind Sail Charters is Chicago’s oldest American Sailing Association sailing school 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.

Best boats, best service, and best location equals the best value in sailing … anywhere!

Sailing image #1Located at Burnham Park Harbor in the heart of Chicago’s famed Museum Campus, Fairwind Sail Charters’ legendary Dragon Fleet features BENETEAU YACHTS with direct walk-on access and ample parking right beside your yacht. With Fairwind Sail Charters, you park, step aboard your yacht, and sail away — that’s the Fairwind Difference.

One of Chicago’s oldest and most respected sailing schools, Fairwind Sail Charters offers award winning American Sailing Association sailing lessons leading to ASA sailing certifications from Basic Keelboat Sailing through Bareboat Charter and Advanced Coastal Navigation. Whether novice or old salt, Fairwind Sail Charters is dedicated to providing you the best sailing instruction to ensure a lifetime of safe and happy sailing.

And when you just want to kick back and enjoy one of the world’s most spectacular sailing venues, Fairwind Sail Charters offers private sailing charters for you and your guests with experienced Master Captains at the helm.

Please take a moment to cruise through what Fairwind Sail Charters has to offer. See for yourself the Fairwind Difference.

If you’re looking for Great People and Great Boats for Great Lakes sailing, join the hundreds of sailors who have made Fairwind Sail Charters their home port!