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Chicago Air Show Charter

Blue Angels fly over Chicago
Blue Angles fly over Chicago, view from the water on a Windy City Sailing charter boat.

The Chicago Air and Water Show is a notorious event that has delighted city visitors for years. With our Chicago sailboat charters, guests will be given a unique opportunity to be right within the action through a fantastic seat located right along the lakefront. Eliminate the frustrations of big crowds and relax in luxury as you watch the show unfold before your eyes.

Your party will have the full Chicago Lakefront as your playground, with spectacular views of the Chicago Air and Water Show.  The yacht is yours for the day, so bring along your family, friends, clients, and any music.  All vessels have the latest safety gear, Bluetooth sound systems, and immaculate bathrooms.

Many of our past Air & Water Show clients opt to cater or pick up prepared foods. You are welcome to bring refreshments of your choice, including alcoholic beverages.  Whole Foods and restaurants are close by for delivery. It’s simple, charming, and EXTREMELY memorable.

What do we need to bring on the sailing charter?

We provide our guests with all the amenities needed to make their night a night to remember. On all of our excursions, guests will be provided with bathrooms, comfortable seating areas, bottled water, ice, and a cooler that can store any of the treats you decide to bring with you on your journey. Feel free to bring along your own music to enhance the viewing experience with surround speakers on the topside. Our experienced crew and captain will handle getting you and your party to the show and you don’t have to worry about anything except for having a good time.

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WINDY CITY SAILING HAS PROUDLY BEEN OFFERING EXCEPTIONAL SERVICE FOR TWO DECADES, AND WE HAVE SATISFIED RETURNING CUSTOMERS TO PROVE IT!

Frequently Asked Sailing Questions

About Our Captains

Our US Coast Guard licensed captains will sail you along Chicago’s skyline in style. Some of our guests enjoy hearing interesting facts about Lake Michigan and our city’s history. But others prefer to enjoy the intimate setting without interruption. Either way, our captain and crew are here to cater to your wishes and ensure that you enjoy every moment of your anniversary charter. 

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