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Welcome to Go Sailing Chicago

Whether you want a romantic sailboat charter for two under the stars, to sail along the Chicago skyline with friends, or learn to sail with the best instructors in the city, Go Sailing Chicago has a Chicago sailboat charter or sailing lesson for you. You can choose from a range of sailboats including cruisers, racers, and luxury sailboats in 3 Chicago locations.

Go Sailing Chicago, LLC, Chicago, IL, 773.710.7245 (SAIL),, copyright 2014,, disclaimer, links

Go Sailing Chicago knows how to play. All private charters are BYOB.

Sail the British Virgin Islands with Go Sailing Chicago! Join in on the 2015 BVI adventure.

All October Charters 20% off!