We Found These Experiences For You (15)
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 ...
2026 Air & Water Show - Special Event!
All ages • 2.5 Hours • Great for friends & family!
Duration 2.5 Hours About An experience you don’t want to miss! Chicago’s famous Air and Water Show aboard the 148′ Lakeshore Sail Charters is truly a magical event. While the official schedule has yet to be announced, we anticipate another year of thrill and excitement. We’ll leave our dock from ...
Chicago
Boat Tour
Tall Ship Windy
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2026 Air & Water Show - Special Event! - Group Rates • 20+ People
All ages • 2.5 Hours • Great for friends & family!
Duration 2.5 Hours About An experience you don’t want to miss! Chicago’s famous Air and Water Show aboard the 148′ Lakeshore Sail Charters is truly a magical event. While the official schedule has yet to be announced, we anticipate another year of thrill and excitement. We’ll leave our dock from ...
Traditional Chicago Blues ~LIVE~ with Michael Charles!!
All ages • 2 Hours • Chase your Monday BLUES away!
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer. About We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the ...
Chicago
2 hours
Kid-Friendly
Boat Tour
Tall Ship Windy
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Traditional Chicago Blues ~LIVE~ with Michael Charles!! - Group Rates • 20+ People
All ages • 2 Hours • Chase your Monday BLUES away!
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer. About We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the ...
Independence Day Weekend Kick Off Sail
All ages • 2 Hours • Best View in the City Aboard 148 foot Schooner Windy
Duration 2 Hours About A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July ...
Chicago
2 hours
Boat Tour
Tall Ship Windy
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Independence Day Weekend Kick Off Sail - Group Rates • 20+ People
All ages • 2 Hours • Best View in the City Aboard 148 foot Schooner Windy
Duration 2 Hours About A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town! Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July ...
Tall Ship Windy 2026 Season Passes / Memberships
Join our membership program and save!
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 ...
Music Memberships
Join our membership program and save!
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 ...
Air & Water Show Top Gun Membership
Join our TOP GUN membership program and get the best seats!
About Top Gun Membership - A 1-day Pass for first boarding of the ship for both Events 10am and 1pm . Very limited - only 15 per day will be sold! You will enjoy first boarding, on each event! There are two events each day, Saturday and Sunday, at 10am and 1pm, each 2.5 hour long. You will be returning ...