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 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.
Power Boat on Lake Michigan
Now in addition to our sailing with us, you can cruise with us on our 40' twin engine Sea Ray Cruiser for power boat enthusiasts. Click on the picture to check out our power boat options. Though sailing is our first passion, sometimes power boating is a nice change.
Power Boat on Lake Michigan
(click here)
$79 Semi-Private Sailing for 2 (60% off)

Up to 45% off Private Sails!
"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