Kevin C.
8/26/2015
I chartered with Windy City Sailing for a noon-time cruise for my wife and me to help celebrate our 30th anniversary. We sailed on a 40 foot motor cruiser, the Jolly Mon, captained by Gentre. We...
Windy City Sailing
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400 W Belmont Ave
Chicago, IL 60657
Windy City Sailing offers luxurious sailing charters in Chicago, accommodating groups ranging from 1 to 10 people. With options for both crewed and bareboat charters, guests can enjoy comfortable amenities, including upscale provisioning and experienced U.S. Coast Guard captains.
Located at Belmont Harbor, just minutes from downtown, Windy City Sailing provides customized sailing experiences tailored to individual schedules. Special events like the Fourth of July Sailing Charter and Navy Pier Firework Charter enhance the unique perspective of Chicago's skyline and festivities from the water.
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Reviews
5.012 reviews
Lisa B.
3/17/2022
Went here for a sunset sail with my boyfriend. Really Enjoyed being able to go on a sail boat. They let volunteers from the crowd pull open the sails. Staff is friendly and funny.
Andrew G.
3/4/2020
Windy City Sailing always exceeds expectations. My family and I look forward to our annual sailing trip w/ Captain Joe and his crew. Even just unplugging on a three hour tour beats some week long...
Ryan K.
9/14/2010
Just booked a 3 hour cruise on their 39' foot boat, and had a blast. Booking was professional and easy and the captain and deckhand were friendly, entertaining and professional. The boat was...
Jenna S.
7/11/2017
Thank you so much for a great sail! Edwina was amazing to work with on logistics in advance of our sail and Captain Marty and crew were so accommodating the day of! We appreciate your efforts to...
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