Chicago Sailboat Charters
Private Charters
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Chicago Sailboat Charters provides the best variety, service, and value for any sailing experience you desire. With many sailboats to choose from, we can arrange the perfect sail to meet your wishes and fit your budget. Whether you are looking for a romantic sailing trip for two, or for a sailboat for up to ten people, we are open every day of the week and will be sailing any time you wish from early in the morning until late at night.
Strictly Sail Chicago
SHOW SPECIALS
Come see us at the Strictly Sail show for fantastic deals
Navy Pier, Jan 26-29, booth 175.
Private Sailing gives your party an opportunity to get away from the crowds, and have a uniquely Chicago experience on Lake Michigan. Your sail with Chicago Sailboat Charters will always have our personal touch, and the first class customer service that keeps our guests coming back.
  • STRICTLY SAIL SHOW SPECIALS
  • 20% off Private Charters
  • Semi-Private Sailing - $100
(Click for details)
"Thank you SO much for everything. I couldn't have pulled it off without you! Marty was wonderful and made planning a breeze. I am very grateful that I chose your company for my first private sailboat charter. We had a fabulous experience. I felt very comforted with Steve's sailing abilities and he was also quite entertaining. Matt's assistance with food delivery and managing the ship was outstanding. My guests and friends were very happy. My maiden sailboat experience was a great success."
- Kira L., Chicago, IL (from YELP!)
Chicago Sailboat Charters   773-236-7245
info2011@ChicagoSailboatCharters.com