Our Fleet

THE LARGEST RENTAL & CHARTER FLEET IN THE MIDWEST

Chicago Sailing has the largest fleet in the midwest and just the keelboat to satisfy your sailing needs! From our zippy J/22’s all the way up to BumbleBee, our largest vessel at 53’, every boat in our fleet is ready for adventure.

You will be safe and secure when you sail with Chicago Sailing. All of our vessels are comfortable and meet stringent U.S. Coast Guard safety requirements.

Call or click today to reserve the vessel of your choice.