Windy City Sailing provides World-Class sailing and power yacht charters for recreational, romantic and educational experiences to individuals and small groups. Private Power Yacht Charters for 1 – 6 Passengers, cruise the Chicago River and the lakefront!
Bed and Breakfast Service on Luxury Sailing Yachts, romantic accommodations paired with sailing in Chicago!
Private Firework Charters at Navy Pier, go sailing off the beaten path and end the day with a spectacular overhead fireworks display. Special Events on Chicago’s Lakefront- Jazz Fest, Blues Fest and Taste of Chicago, rent a yacht and arrive in style!

July 4th Fireworks – Chicago Air & Water Show both are major Chicago attractions best enjoyed on a Lake Michigan cruise! Celebrations and Once-in-a-Lifetime Events, birthdays, anniversaries, proposals, family reunions, and other very special occasions .
Gain another outlet to the wonderful Chicago lakefront while discovering the beauty of Lake Michigan from a different view! We took the family out with Windy City Sailing for an afternoon on the water to celebrate Grandma’s birthday.
Thanks Liz, glad the family had a great time…look forward to sailing with you again next season!

Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom yachts.

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