Chicago Sailboat Charters: Your Gateway to Marine Careers

Charter a boat in Chicago with us. When you rent a boat from Chicago Sailboat Charters, we provide the best variety, service, and value for any charter or rental boat experience you desire. With several sailboats and power boats, as well as our 36 passenger Big Boat, 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, a sailboat for up to 11 people, power boat rental for up to 12 people, or a party boat rental for up to 36, we are open every day of the week and we are on the water from early in the morning until late at night. If you are looking for a Chicago boat rental with captain, we are the charter boat company or you.