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Private Charters & Weddings in Chicago

A Beautiful Stage for Your Event

Set sail on Windy for weddings, parties, corporate functions, reunions, church outings, tour groups, team building, and more! Windy can be chartered for a maximum of 148 guests.

Envision your picturesque, romantic event on a majestic tall ship with the backdrop of one of the world’s most beautiful cities. Plan now for your chance to host a memorable Chicago wedding and for memories that will last a lifetime. Tall Ship Windy can offer you just that.

You can enjoy a remarkable backdrop with a royal touch: Rejuvenating beauty treatments to pamper yourself with VIP flair before your ceremony. We can help you capture the picture-perfect moments with our experienced wedding and yacht photographers. The Windy will be your chic 148-foot Tall Ship for your ceremony; she has all the character and charm of the great days of sailing. Windy is silently pushed by the winds once her sails are set and engine turned off, to create tranquility for your event.

All you need to do is pick the date, and the ceremony will take place on beautiful Lake Michigan aboard the Tall Ship Windy. You could be wed on the ideal romantic venue with up to 150 guests on board Download the Fact Sheet here.


  • No alcohol can be included with catering as Windy is a registered bar and is licensed to accept and distribute only its own alcohol. Beverage services starting at $12/per person/per hour.
  • All catering vendors must be approved by Windy’s management before they can be hired. Please ask us for a list of our preferred caterers.
  • There is an additional charge for entertainment.


Windy boasts three spacious decks, a grand salon, and a bar for your enjoyment. With plenty of benches and deck boxes, there is plenty of seating available. Our bar is stocked with soda, water, beer, wine, liquor, and snacks. Ask us about our bar packages! We feature brands from local distilleries and wineries.


Caterers generally set up buffet-style in the grand salon, adjacent to the galley area, with guests free to move in and out. Seating is informal on the Windy, so “picnic-style” meals work best. All catering vendors must be approved by Windy’s management before they can be hired.


With a storyteller on board, choose from programming options such as Chicago Architecture, Piracy on the Great Lakes, and more. Live music is also available; or, bring your own band on board.

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