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Tall Ship Windy

Chicago Skyline Sails & Tours

Anchor View All Sails

For public health and safety, Windy is temporarily not accepting cash for ticket purchases, or purchases at the bar and ship’s store. However, cash gratuities are welcome for the ship’s crew and bartender. 

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Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water.

Hour Glass 75 Minutes | Starting at $37

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Welcome Aboard Tall Ship Windy

The Tall Ship Windy, located on Chicago’s Navy Pier, brings you exciting boat tours that are educational, creative, and inspiring. From our daily storytelling adventures and field trips for students to our concert sails, there is something for everyone. Come enjoy the Chicago skyline as you sail on our tall ship!

For groups or charters, email us at [email protected] or call us at: (312) 451-2700

Illustration of fireworks

The Tall Ship Windy offers the most spectacular fireworks experience during the Chicago summer.

Illustration of pirate hook

Our sails are both fun and educational, which makes them the perfect way to see Lake Michigan.

Illustration of sailing ship

Feel the spirit of centuries past and hoist the sails as part of your experience on Tall Ship Windy.

Illustration of Chicago skyline

There is simply no better way to experience Chicago’s world-famous skyline than on the Tall Ship Windy.

Catch these five-star reviews from TripAdvisor!

Deb R profile photo
A fantastic cruise!

We went on the "pirate" cruise. They told tales of actual Lake Michigan pirates and made it very entertaining for the kids and the adults. I want to go on this cruise again!

– Deb R., TripAdvisor
Ron F profile photo
Great way to end the summer

We went on the Lakeside Architecture Tour. It was a very educational and relaxing seventy-five minutes. I highly recommend the experience.

– Ron F., TripAdvisor
Daniel C profile photo
Always a good time

I've set sail on Tall Ship Windy 4-5 times over the past few years, and it is always a good time. You get a nice view of the city and the crew is entertaining and knowledgeable.

– Daniel C., TripAdvisor
Tina B profile photo
Incredible Experience

If you want humor, entertainment, and an inclusive experience for young and the old, don’t miss this! I appreciate everything about this adventure, and Austin you’re the best!

– Tina B., TripAdvisor
A Sailing We Will Go!

Had a wonderful sail on a chilly, overcast night! Crew was professional, friendly and informative. Would recommend this trip to anyone, so relaxing. Oh, used a Groupon, an extra bonus!

– Cathy B., TripAdvisor
Sunset over the city

Best view of the city! Highly recommend the 7pm sail to watch the sunset between the buildings. Fun and knowledgeable crew made the Windy the highlight of our Chicago visit.

– Lance B., TripAdvisor