Sailing Trips in Chicago
Top 5 Best Chicago Sailing Trips
Found 3 Sailing Trips activities in Chicago. Sort by Popularity.Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
(4.7 of 32 reviews)
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More
Start From $91.23
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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Chicago
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Superb32 reviews4.7
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
Start From $91.23
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
(5 of 73 reviews)
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More
Free Cancellation
Private Tour
Private Tour
Start From $507.96
Likely to Sell Out Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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Chicago
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Superb73 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Free Cancellation
Private Tour
Private Tour
Start From $507.96
Chicago's Fireworks Show aboard Tall Ship Windy!
(4.7 of 26 reviews)
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More
Free Cancellation
Private Tour
Private Tour
Start From $113.73
Likely to Sell Out Chicago's Fireworks Show aboard Tall Ship Windy!
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Chicago
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Superb26 reviews4.7
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Free Cancellation
Private Tour
Private Tour
Start From $113.73