Fairwind Sail Charters

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.

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

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

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

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

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

02/21/2024

Spring 2024 is only a month away and sailing is not far behind! Fairwind Sail Charters offers a beautiful all-Beneteau fleet for sailing on Lake Michigan. Contact Fairwind now to learn more about Chicago’s original and still best sailing yacht lease share program. Sign up now and get a free additional sail! Or, if you are new to sailing, take advantage of Chicago’s oldest American Sailing Association certified sailing school. Fairwind will have you at the helm with expert instruction to get you started right on your sailing adventures. Call or email today to learn more about the Fairwind Difference!

02/05/2024

Sailing downwind with Jill Mateo from Virgin Gorda to Norman Island in the British Virgin Islands. Reefed jib doing 8 knots. One of my best sails down there. This was my 21st trip!

05/11/2022

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.

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...