Fairwind Sail Charters

Fairwind Sail Charters Chicago's Oldest American Sailing School, Sailing Club and Premier Yacht Lease Share Program, Private Sailing Charters

Located in Burnham Park Harbor, Fairwind Sail Charters is Chicago's oldest American Sailing Association certified sailing school, and premier Sailing Yacht Lease Share Program. It also offers the best in private sailing charters and corporate events. Serving today's active, value-conscious sailor, Fairwind Sail Charters has been Chicago’s sailing standard since 1978. Beautiful yachts, unparalleled personal service, and the best rates anywhere have made Fairwind Sail Charters’ Sailing Yacht Lease Share Program the choice of Chicagoland sailors for over three decades. Fairwind's legendary “Dragon Fleet” features Beneteau yachts with walk-on slip access, ample parking, and the safest, most convenient location in Chicago sailing. With Fairwind Sail Charters you sail a meticulously maintained and outfitted yacht all season long for a fraction of what it costs to rent or own. One of Chicago's most respected sailing schools, Fairwind Sail Charters offers award winning American Sailing Association certified sailing instruction from Basic Keelboat and Basic Coastal Cruising through Bareboat Charter and Advanced Coastal Navigation. From novice to old salt, Fairwind Sail Charters is dedicated to providing you the best sailing instruction possible to ensure a lifetime of safe and happy sailing. When you just want to kick back and enjoy one of the world’s most spectacular sailing venues, including Chicago’s special summer events like fireworks or the Air and Water Show, Fairwind Sail Charters offers private sailing charters with experienced Master Captains at the helm. And for a corporate outing or team building experience you will never forget, make Fairwind Sail Charters your home port!

08/29/2026

There is nothing like sailing along Chicago’s magnificent lakefront. Get to know Fairwind Sail Charters.

A beautiful day in Chicago always makes these sparkle a little brighter ✨ Meet our Dragon Fleet, featuring four beautifu...
08/27/2026

A beautiful day in Chicago always makes these sparkle a little brighter ✨ Meet our Dragon Fleet, featuring four beautiful Beneteau yachts.

08/27/2026

Get started with sailing! Fairwind offers award-winning instruction and personalized scheduling from friendly, straight-talking folks.

05/18/2026

Sign up for one of our luxury yachts and you’ll feel like you own it. That’s the Fairwind difference!

05/06/2026

After almost 50 years in operation, it’s finally time to post something on Instagram.

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing ce...
02/25/2026

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 as we take another step closer to our Golden Anniversary in 2028. Fairwind is Chicago’s oldest sailing business and offers the best sailing program anywhere. Beautiful boats and exceptional customer service is the Fairwind Difference. Isn’t it time for you to join the Fairwind sailing family? Sign up before April 15 and get a free additional sail on us!

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 a

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing ce...
02/25/2026

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 as we take another step closer to our Golden Anniversary in 2028. Fairwind is Chicago’s oldest sailing business and offers the best sailing program anywhere. Beautiful boats and exceptional customer service is the Fairwind Difference. Isn’t it time for you to join the Fairwind sailing family? Sign up before April 15 and get a free additional sail on us!

Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 a

After a wonderful summer of sailing, Fairwind Sail Charters is already looking forward to summer 2026 as we take another...
09/23/2025

After a wonderful summer of sailing, Fairwind Sail Charters is already looking forward to summer 2026 as we take another step closer to our Golden Anniversary in 2028. As Chicago’s oldest sailing business and premier lease share program, Fairwind thanks the mighty Dragoneers for their friendship and support over the years. Isn’t it time for you to join the Fairwind sailing family? Our lease share program is unlike any other. Contact us now to learn about the Fairwind Difference that always puts your safety first.

After a wonderful summer of sailing, Fairwind Sail Charters is already looking forward to summer 2026 as we take another step closer to our Golden Anniversary i

As we enter the dog days of summer, it is worth emphasizing the value of Fairwind Sail Charters business model that is b...
08/05/2025

As we enter the dog days of summer, it is worth emphasizing the value of Fairwind Sail Charters business model that is based on seamanship. Fairwind Sail Charters is the only lease share program that provides makeup sails for sails missed due to bad weather. Fairwind provided makeup sails earlier this summer when Chicago had excessive heat, and even for several days when there was practically no wind. Fairwind never wants to put a financial pressure on a skipper to sail in poor or questionable conditions. Fairwind schedules its boats so there is plenty of open time to supply safe, pleasurable sailing for its dear Dragoneers. That's just one more example of the Fairwind Difference:

Sailing is Fairwind's full-time business, not a freelance sideline, and its customer service is unequaled. Over 90% of Fairwind skippers are repeat customers, m

Thank you to the amazing Dragoneers for a great summer of sailing. With Fall in the air, it’s never too soon to start th...
09/27/2024

Thank you to the amazing Dragoneers for a great summer of sailing. With Fall in the air, it’s never too soon to start thinking about next year! Please contact us if you would like to know more about our American Sailing Association certified sailing school or our premier sailing yacht lease share program. Come sail with us and experience the Fairwind Difference!

Thank you to the amazing Dragoneers for a great summer of sailing. With Fall in the air, it's never too soon to start thinking about next year! Please contact u

Address

Burnham Harbor
Chicago, IL
60605

Telephone

+17084422670

Website

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