Sailing through Time and Waves: Aboard Tall Ship Windy in Chicago

View of the Chicago skyline at twilight from the decks of Tall Ship Windy

Chicago, a city known for its magnificent skyline, rich history and stunning lakefront, offers a unique experience that combines all of these elements in a truly memorable way. Aboard Tall Ship Windy, visitors will embark on a voyage that takes them back in time while enjoying the modern marvel that is Chicago’s skyline. In this blog, we’ll explore the captivating world of boat cruises on Tall Ship Windy in the Windy City.

Posted in:
Lake Michigan Boat Charters

Great for Children!

From $25 per Person

90 Minutes

Educational Sail: Tall Ship Discovery Sail

History comes alive on this exciting Windy City boat tour. Enjoy an educational adventure for curious minds of all ages with the backdrop of the iconic Chicago skyline always in view. Led by our crew-educators, experience a hands-on sailing excursion in Chicago aboard Windy.

Book Now

Learn More

Frequently Sells Out

From $49 per Person

75 Minutes

Chicago Skyline Sunset Sail

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

Book Now

Learn More

Most Popular!

From $39 per Person

75 Minutes

Chicago Skyline Sail Aboard 148' Tall Ship Windy

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

Book Now

Learn More