Chicago Skyline Sails & Tours

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Sails Offered Daily

Chicago’s Official Tall Ship

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Lakeside Architecture Sail

Most Popular!
75 Minutes

Standard Boarding
Adults (Ages 13+) $37 | Child (Ages 0-12) $14 

VIP Captains Boarding
Adults (Ages 13+) $44 | Child (Ages 0-12) $20

Departs 11am & 5pm 7 Days a Week

Take in Lake Michigan and one of the world’s most famous skylines on Chicago’s official Tall Ship. Our crew today explores Chicago’s architectural majesty while Windy sails across our beautiful lakefront skyline.

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Skyline Sail with Tales of Real Pirates of the Inland Seas

Learn About Lake Michigan with the Real Pirates of the Inland Seas.

Learn about real pirates of Lake Michigan
Offered Daily
75 Minutes

Skyline Sail with Tales of Real Pirates of the Inland Seas

Learn About Lake Michigan with the Real Pirates of the Inland Seas.

Learn about real pirates of Lake Michigan

From $37 Learn More »
Offered Daily
75 Minutes
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Skyline Sail

Discover the famous Windy City from the water!

Offered Daily
75 Minutes

Skyline Sail

Discover the famous Windy City from the water!

From $37 Learn More »
Offered Daily
75 Minutes
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Special Events

Fireworks Cruise

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Upcoming Limited Time Cruises

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Concert Series

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About Tall Ship Windy

Tall Ship! Since 1996, we‘ve been sailing from Navy Pier in Chicago and have hosted thousands of happy sailors since.

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

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

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

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

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

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

There’s just no way to see Chicago’s world-famous skyline than on the Tall Ship Windy.

There’s just no way to see Chicago’s world-famous skyline than on the Tall Ship Windy.

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“Great way to see the city!

Seeing the city from the Lake was a unique experience for my mother and I (Chicago Natives). We learned a lot about the city we thought we already knew a lot about! Would highly recommend for kids as well! We got to see the eclipse while aboard which was a lot of fun. The whole staff was friendly and helpful, and the ship is beautiful!”

-TripAdvisor Review

Tall Ship Windy Chicago
Phone (312) 451-2700
Map Marker

600 East Grand Avenue, Navy Pier Chicago, IL, 60611
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