Chicago Sailboat Charters
faq & terms
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.
New for 2013, in addition to our Sailboat offerings, we now have a 40' twin engine Sea Ray Cruiser for power boat enthusiasts. Click on the picture to check out our power boat options.
Navy Pier Chicago Fireworks Sailing
Daytime Sailing Trips
Night Sailing and Full Moon Risings
50% off ALL Private sails
this Sunday and Monday only.
Call to reserve
"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 (
Chicago Sailboat Charters 773-236-7245