Special Event Sails in Chicago, IL

The thrill of the Chicago Air & Water Show returns to the Lake Michigan lakefront this year beginning at 9AM on Saturday, August 20 and on Sunday, August 21, 2022.

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. 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.

This is the don’t miss sail of the year, Tall Ship Windy’s Labor Day End of Summer Celebration Sail. Departing from Navy Pier at 8:45pm, celebrate Labor Day, and for some the end of Summer, with your friends and family aboard the famous 148′ four-mast schooner S/V Windy.