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All Sails in Chicago, IL

Browse our sails below and book your Chicago Sailing Adventure today!

From $39 per Person

Watching Fireworks on Wed and Saturday night has become a Chicago tradition. And, there is no better seat in the house than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago.

Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.

The Wednesday Fireworks Boat Tour departs promptly at 8:45pm. The Saturday tour starts promptly at 9:15pm.

From $79 per Person

Chicago’s famous 2 hour Pirates Pub Sail departs every Friday night at 9pm aboard Tall Ship Windy at Navy Pier. Yes, this is Chicago’s Famous and Only Floating Pirates Pub!

Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. Your ticket includes up to four complimentary beverages; beer, soda or water, per person.   You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan.  Chicago’s famous Pirates Pub Sail is an event that should not be missed.

  • VIP Event, 1 Night Only
From $119 per Person

A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seat in town! Order a cool drink from our bar, then relax, and enjoy a leisurely evening watching the best Fireworks display in the city.

Chicago’s Fourth of July fireworks is one of the best in the nation. Enjoying this event from Chicago’s official Schooner, Tall Ship Windy, is truly a VIP event. This event sells-out early. For 2022, Chicago’s 4th of July Weekend Fireworks Will Be On Monday July 4th.


Are you looking for a relaxing sail along the Lake Michigan lakefront? Are you interested in an educational tour featuring stories from Chicago’s unique history? Or maybe you would prefer to enjoy a drink or two while watching a thrilling fireworks display over the stunning Chicago skyline? Let Tall Ship Windy be your guide!