Fairwind Sail Charters

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!

Spring into sailing for summer 2026 and get a free additional sail! – Fairwind Sail Charters, Inc. 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 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!

Spring into Sailing for Summer 2026 and get a free sail! – Fairwind Sail Charters, Inc. Fairwind Sail Charters is accepting applications for its premier sailing lease share program and its American Sailing certified sailing school for summer 2026 a

Entering its 44th year as Chicago's premier sailing yacht lease share program, and Chicago's oldest American Sailing Association certified sailing school, Fairwind Sail Charters is ready to get you on the water this summer. Whether it is sailing instruction or a private sailing charter with family and friends, Fairwind offers the best and safest sailing experience in Chicago. Contact us to learn more about our programs and find out why Fairwind Sail Charters has been the choice for discerning sailors for over four decades.

Fairwind Sail Charters Welcomes Summer 2022! - Fairwind Sail Charters, Inc. Entering its 44th year as Chicago’s premier sailing yacht lease share program, and Chicago’s oldest American Sailing Association certified sailing school, Fairwind Sail Charters is ready to get you on the water this summer. Whether it is sailing instruction or a private sailing charter with fami...