We Found These Experiences For You (8)
Tall Ship Windy
Chicago Skyline Sail
All ages • 75 Minutes • Great for friends & family!
Duration Each sail is approximately 75 minutes. About AVAILABLE NOW SAIL DAILY MAY THROUGH SEPTEMBER! Leave the hustle and bustle behind! Explore Chicago’s shoreline, with a leisurely trip on Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the ...
Chicago
75 minutes
Boat Tour
Tall Ship Windy
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Chicago Skyline Sail Group Rates • 20+ People
All ages • 75 Minutes • Great for friends & family!
Duration Each sail is approximately 75 minutes. About AVAILABLE NOW SAIL DAILY MAY THROUGH OCTOBER 1! Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from ...
Fireworks Cruise!
All ages • 90 Minutes • Great for friends & family!
Duration 90 Min. The Wednesday Fireworks Boat Tour starts promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm. About A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely ...
Chicago
90 minutes
Boat Tour
Tall Ship Windy
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Fireworks Cruise! - Group Rates • 20+ People
All ages • 90 Minutes • Great for friends & family!
Duration 90 Min. The Wednesday Fireworks Boat Tour starts promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm. About A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Grab a cool drink from our bar, relax, and enjoy a leisurely ...
Tall Ship Windy 2026 Season Passes / Memberships
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About Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship throughout our sailing season. Once you purchase your membership, join us during our Skyline Sails throughout the sailing season for no additional cost. After purchasing your membership, you’ll receive a unique membership ...
Gift Card
A gift for an unforgettable experience!
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Chicago
Gift Card
Tall Ship Windy
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Music Memberships
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About NEW 2026!! Music Memberships - Two options Monday Night Music, With Michael Charles Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship throughout your sail, with live music! Once you purchase your membership, join us during our Live Music Concert Sails throughout the ...
Wednesday Night Fireworks Memberships
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About NEW 2026!!! We are now offering two VIP/Admiral Membership options, for our Wednesday Night Fireworks! While every sail enjoys the beautiful Chicago lakefront and skyline from your favorite tall ship throughout our sailing season, this night sailing is especially memorable. Once you purchase your ...