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Group Sales

Group Sales and Discounts

Make your next group outing unique with a real tall ship sailing adventure! Tall Ship Windy is a majestic 148-foot four-masted gaff topsail schooner. Modeled after a traditional Great Lakes trading ship, she is built of modern materials but boasts all the character and charm of the Golden Age of Sail.

Download Small Group Sales Fact Sheet: Small Group Sales Inquiry

Download Charter Fact Sheet: Windy Charter Inquiry Document

Group Events

Bring your family trip, reunion, retreat, happy hour, or celebration to Windy! Whether you’re looking for hands-on adventure, intriguing history, or a leisurely cruise, Windy has something for you!

Education Sails

Please visit our Educational Sails page for more information on setting up an educational sail for your school field trip or educational group.


Windy boasts three spacious decks, a grand salon, pressurized “heads” (marine toilets), and a bar for your enjoyment. Plenty of deck seating is available on benches and boxes. The bar is stocked with soda, water, beer, wine, liquor, and snacks. Ask about our bar packages! We feature brands from local distilleries and wineries.


Windy’s signature programming combines exciting Great Lakes history with interactive storytelling for curious minds of all ages. Our knowledgeable docents bring the history life, so you can experience Chicago like never before! On Windy, explore Chicago architecture, piracy on the Great Lakes, Chicago, maritime ghost stories, and more.


Discounts are applied according to the following fee schedule.

Group Size: Discount:

  • 20-39 10%
  • 40-59 15%
  • 60 or more 20%

Private Charters

Please visit our private charters page for more info or download our charters fact sheet here.


Contact us at (312) 451-2700 for private charter pricing, scheduling, and more information.

Book Today!

To book your adventure, or to get more information, contact us via email at [email protected] or via phone at (312) 451.2700