Sailing Trips in Chicago
Top 10 Best Chicago Sailing Trips
Found 6 Sailing Trips activities in Chicago. Sort by Popularity.Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
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
Private Tour
Likely to Sell Out Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago
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Chicago
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Superb27 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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
Private Tour
Likely to Sell Out Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
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Chicago
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Superb70 reviews5
Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....
Private Tour
Chicago's Fireworks Show aboard Tall Ship Windy!
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
Private Tour
Likely to Sell Out Chicago's Fireworks Show aboard Tall Ship Windy!
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Chicago
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Superb14 reviews4.8
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Private Tour
Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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
Private Tour
Likely to Sell Out Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"
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Chicago
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Superb20 reviews4.8
Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....
Private Tour
Chicago Air and Water Show VIP Cruise or Skydeck Experience
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More
Private Tour
Likely to Sell Out Chicago Air and Water Show VIP Cruise or Skydeck Experience
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Chicago
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Superb2 reviews5
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....
Private Tour
Likely to Sell Out Monday Night Concert Series: Blues and Views Aboard Tall Ship
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Chicago
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Superb2 reviews5
Book early, as these tend to sellout! you are free to move about the ship, while the music plays, ev....
Private Tour