Chicago’s skyline was built to be admired from the water — and Tall Ship Windy turns that view into an unforgettable sailing adventure. Windy is Chicago’s official tall ship ambassador, a majestic four-masted schooner gliding across Lake Michigan with the city’s towers glittering on the horizon.
This is sailing the fun way. You can join the friendly crew and help raise one of Windy’s many sails, or simply relax on deck and let everyone else do the work while the breeze and the views do the rest. Fun for all ages, with a full bar and a gift shop on board to complete the experience.
Travelers rate the Chicago Skyline Sail 4.7 out of 5, and tickets start at $91.23. Morning, afternoon, and sunset departures make it easy to fit this floating postcard into any Chicago itinerary — just book ahead, because a tall ship this beloved fills up fast.
Ready for the Windy City’s most romantic ride? Book this tour on Viator
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Photo: Viator
