CHICAGO'S TOP BOAT RENTALS

Chicago's Best
Sailboat &
Yacht Rentals

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!

BIG BOATS

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SAILBOATS

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PREMIUM YACHTS

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LUXURY YACHTS

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Why Chicago Sailboat & Yacht Charters?

Chicago Sailboat & Yacht Charters offers Chicago’s largest variety of captained charters for sailboats, yachts, and spacious big 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.

“We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite easy through the website, then you can contact the captain yourself to see who is available (company gives names/contact info). I would definitely rent from CSC again. Prices were also pretty average compared to other companies! Definitely recommend. “

Gabrielle W.

“Captain Rob and Jill were great. Everything ran like clockwork and they were accommodating on the boat. Great conversationalists as well. I appreciated the simplicity of booking and acquiring their services. It felt a little too easy to be true but it was. They just have an efficient and fun operation. Thanks captain Rob and Jill!”

“After doing a ton of research, I came upon Chicago Sailboat Charters. I found them through their amazing reviews and recommendations. They were quick to respond and answered all of my questions. I ending up booking a Cruiser Class Power Boat for a bachelorette party of 11 girls.”

Lindsey S.