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!
  • 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 .

Specializing in Proposals | Gift Certificates for All Events


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

5 Responses to Welcome to Windy City Sailing – 773.868.0096 – Chicago Sailboat and Power Yacht Charters

  1. Dee Harrison says:

    We went out yesterday for a three hour charter and had a fantastic time! The weather for FANTASTIC (for Chicago) and the yacht and captain from Windy City Sailing could not have been better! A+ with FOUR STARS! Will go again soon
    – Dee

  2. Elizabeth says:

    We took the family out with Windy City Sailing for an afternoon on the water to celebrate Grandma’s birthday. She was very nervous starting out but the whole trip was fantastic. The crew was hospitable, personable, and very knowledgeable. They took great care of us and we felt safe the whole time. The boat was amazing and the facilities fantastic. The grandkids are still talking about how much fun they had hanging out on the boat and grandma is ready to go back out again soon. Thank you.

  3. Robert liska says:

    Five star experience. Gone four times and will keep going. The staff and captains r a plus. Took my 90 year old mother and she said it was an item on her bucket list.

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