CHICAGO'S #1 BOAT RENTAL FOR OVER 17 YEARS

Power boats can be the perfect summer time Lake Michigan party boat! Make it a crowd of up to 11 people, so you can enjoy the ample seating for 11 in the cockpit / party deck. There is a huge area for sunbathing on the bow. Guests on board can cool off swimming in the lake and then dry off on the bow under the season’s blue skies. Our 40′ cruisers also feature a easy access ladder to get back onto the vessel.

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OUR FLEET

OUR BOAT RENTALS ARE PERFECT FOR EVENTS OF ALL KINDS

SWIMMING & PLAYPEN

The Chicago skyline is spectacular from the water. Cruising towards Navy Pier, or straight out from the shoreline, the views cannot be matched.

NIGHTIME & FIREWORKS

The sun sets behind the Chicago skyline and a glow comes up from behind the buildings, followed by the skyline lighting up once the sky gets completely dark.

CHICAGO RIVER CRUISES

The Chicago skyline is spectacular from the water. Cruising towards Navy Pier, or straight out from the shoreline, the views cannot be matched.

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HOW TO BOOK YOUR BOAT RENTAL ONLINE

Step 1: Use our online booking platform (click HERE) to select your date and view charter availability.

Step 2: Select your charter and complete your reservation online in under 60 seconds.

Step 3: Once booked, check your confirmation email for detailed instructions on securing a captain.

WHY CHICAGO BOAT RENTALS?

Chicago Sailboat Charters provides the widest selection of captained charters in Chicago, featuring sailboats, yachts, and spacious vessels for groups ranging from 1 to 36. Whether you're seeking a daytime sail, a breathtaking sunset cruise, a relaxing swim and sunbathe experience, or a front-row seat to Navy Pier's spectacular fireworks, we have the perfect option for you.

TESTIMONINALS

Neekta S.

SO MUCH FUN!!

How it works: You charter a boat along with the captain and crew. The boats are owned by the company.

We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person.

We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS.

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Lindsey S.

The best boating experience ever!!!

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. After booking, you receive a list of captains to choose from and I chose Gregg after reading countless, 5-star reviews!

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Gabrielle W.

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.

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Logan C.

I contacted Captain Marty at Chicago Sailboat Charters to arrange for a private charter to celebrate our wedding anniversary. The booking online feature was appealing to me, because often times it's hard for me to use the phone during the day. He's also very knowledgeable of sailing, Lake Michigan and the city of Chicago.

Our sailing trip was a blast, I'd highly recommend Marty and Chicago Sailboat Charters.

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Neekta S.

SO MUCH FUN!!

How it works: You charter a boat along with the captain and crew. The boats are owned by the company.

We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person.

We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS.

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Lindsey S.

The best boating experience ever!!!

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. After booking, you receive a list of captains to choose from and I chose Gregg after reading countless, 5-star reviews!

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