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 19 and on Sunday, August 20, 2023.

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.

Tall Ship Windy’s Memorial Day Start of the Summer Celebration . Departing from Navy Pier 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.