CHICAGO'S TOP BOAT RENTALS

When you rent a boat from Chicago Sailboat & Yacht Charters, we provide the best variety, service, and value for any charter or rental boat experience you desire.

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CHICAGO'S TOP SAILBOAT & YACHT RENTAL

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!

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HOW TO BOOK YOUR BOAT CHARTER ONLINE

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.

WHY CHICAGO SAILBOAT CHARTERS?

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.