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, Chicago Sailboat Charters & Rentals has the perfect charter for you, every day of the week!
Step 1: Use our online booking platform (click HERE) to select your date and view charter availability.
Step 2: Once you select your charter, reserve and pay directly online in less than 60 seconds.
Step 3: After booking, refer to your confirmation email for instructions on how to book a captain.
Chicago Sailboat Charters offers Chicago's largest variety of captained charters for sailboats, yachts, and spacious boats, accommodating groups of 1 to 36 people. Enjoy daytime sailing, sunset cruises, swimming and sunbathing sails, or even witness the spectacular Navy Pier fireworks from our boats.