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WELCOME TO WINDY CITY SAILING – 773.868.0096 – CHICAGO SAILBOAT AND POWER YACHT CHARTERS

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PRIVATE SAILING AND POWER YACHT CHARTERS ON THE CHICAGO LAKEFRONT

Windy City Sailing provides World-Class sailing and power yacht charters for recreational, romantic and educational experiences to individuals and small groups. Experience the thrill of sailing and Chicago sightseeing with United States Coast Guard certified captains on our custom yachts. Our charters are personal and private for your group, family or clients.

WINDY CITY SAILING PROVIDES THE FOLLOWING SERVICES ON LAKE MICHIGAN:

  • Private Sailboat Charters for 1 – 6 Passengers,  our lakefront is the number one “Chicago tourist attraction”
  • Private Power Yacht Charters for 1 – 6 Passengers, cruise the Chicago River and the lakefront!
  • 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 .

Specializing in Proposals | Gift Certificates for All Events

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