Chicago Sailing

Explore Chicago sailing tours including skyline sails, fireworks cruises, and private charters on Lake Michigan with Tall Ship Windy and more.

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Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats

★ 4.7 (26)

From $113.73 USD

Navy Pier Chicago: Private Sailboat Charter with Captain

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate a

★ 5.0 (1)

From $1,399.00 USD

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed capt

★ 5.0 (73)

From $507.96 USD

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lak

★ 4.7 (32)

From $91.23 USD