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Welcome to Windy City Sailing, providing Chicago sailboat charters and power yacht charters l

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Windy City Sailing provides World-Class private sailing and power yacht charters for parties up to 10 people. Our yachts are available for social and romantic experiences to singles, couples and small groups on Lake Michigan. Our yachts are first class with United States Coast Guard Captains who are personal and ensure your safety.

Windy City Sailing provides many options for your yachting pleasure. The most popular excursions are the private sailboat charters for 1-10 passengers and the power yacht charters for 1-6 passengers.  Our sailing and power yacht firework charters to Navy Pier provide spectacular overhead displays on Wednesday and Saturday nights. Major attractions include July 4th fireworks, Chicago Air & Water Show, Jazz Fest, Blues Fest and Taste of Chicago.  The best way to see Chicago is on a Lake Michigan cruise so charter a yacht and arrive in style!

Special occasions and holidays become fantastic when enjoyed on a yacht. Proposals, family reunions, marriages, birthdays, and other celebrations are memorable with Windy City Sailing!

Our sailing yacht, Nebula is a Beneteau 393, a 40 feet sloop-rig sailboat that is praised for its comfort and performance.  The owner’s stateroom and large salon make Nebula perfect for Chicago and Lake Michigan sailing charters.

Jolly Mon is a 38’ Sea Ray Sun Dancer, and ready to cruise Lake Michigan and the Chicago River.

Enjoy the Wednesday and Saturday night Fireworks display at Navy Pier. Explore the sites of the Chicago River and views of the Chicago Skyline. Relax and enjoy a day or evening on Lake Michigan.

Experience the thrill of Chicago Sailboat Charters on our custom sailing and power yachts.

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Gain another outlet to the wonderful Chicago lakefront while discovering the beauty of Lake Michigan from a different view!