Skip to primary navigation Skip to content Skip to footer

All Sails in Chicago, IL

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

  • VIP Event - One Day Only!
From $49 per Person

A one day, VIP event.  Moonlight Sail Aboard Tall Ship Windy.

Tall Ship Windy’s Memorial Day Start of Summer Celebration. Departing from Navy Pier on Sunday May 26th at 8:45pm, celebrate Memorial Day and begin the summer with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.

Sailing Lake Michigan aboard Chicago’s official flagship Tall Ship Windy is a Chicago tradition.  Enjoying a night time sail and experiencing a moonlit Chicago skyline is truly phenomenal.  Join us for this special, one day only Memorial Day sail.  And, bring your camera!

From $59 per Person

There is something special about sailing in Chicago combined by kicking off your week and joining us for a 2-hour concert sail. This Navy Pier boat tour sails from 7pm-9pm every Monday this summer. We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago at sunset from the waters of Lake Michigan, accompanied by the sweet sounds of the blues.

  • Every night at 5pm!
From $39 per Person

Enjoy happy hour drink specials onboard this Navy Pier Boat Tour every night at 5pm and experience breathtaking views of the Chicago skyline from the water! It’s the perfect way to end your workday or kick off your weekend plans. Learn about the people, plans and persistence that shaped Chicago’s most famous sights and join us on the main deck to enjoy the lively narration and an Architectural Tour of Chicago from the water.

From $69 per Person

Sail into the night and embark on a two-hour party sail from Navy Pier; join us for Chicago’s only Pirates Pub. Sail onboard a 148-foot Tall Ship in the Windy City! This popular Chicago event is one you will not want to miss; it is unlike all other boat excursions in Chicago. Enjoy an onboard DJ and the wind in your hair as you dance the night away with the mesmerizing Chicago skyline as your backdrop. Sing along to traditional pirate tunes and your favorite party anthems while soaking in the breathtaking sights on Lake Michigan.

From $50 per Person

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show 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.

  • VIP Event, 1 Night Only
From $89 per Person

A SPECIAL EVENT SAIL! Treat yourself to an Independence Day Sail from the best seat in town!

Order a cool drink from our bar, then relax and enjoy a leisurely evening listening to patriotic music and enjoying the Chicago skyline. The City of Chicago MAY also have fireworks on July 4th, but officially this has not been announced. Chicago’s Fourth of July celebration 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.


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!