Chicago Boat Rental

Captained Sailboats & Yachts in Chicago

Ready to get out on the water? Chicago Boat Rental makes it simple to book a private, captained boat charter with clear pricing and a live availability calendar.

Choose a sailboat, yacht, or party boat for sightseeing, celebrations, or a relaxed cruise—then bring your favorite snacks and drinks and let your captain handle the rest.

39ft SAILBOATS

12 GUESTS

BELMONT HARBOR

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46ft LUXURY YACHTS

13 GUESTS

DUSABLE HARBOR

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40ft PREMIUM YACHTS

13 GUESTS

DUSABLE HARBOR

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50ft BIG BOAT

36 GUESTS

DUSABLE HARBOR

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“I mean, water sports are the best. Chicago Boat Rentals has fair prices and nice boats (not old and beat up). I’ve been here multiple times and always bring friends from out of town.”

Felice G.

“The best boat rental in Chicago! We had a great time on their newest yacht the 46′ ft one. Would highly recommend booking!”

Archal R.

“Had an amazing experience with Chicago Boat Rentals! The crew was super professional, friendly, and so accommodating the entire time. They made sure everything ran smoothly and my group had an extremely fun and memorable day on the water. From start to finish, it was nothing but good vibes. I’ll definitely be booking with them every time I’m in Chicago. Highly recommend!”

Paulina N.

Chicago Boat Rentals are perfect for:

Swimming and Playpen

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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Corporate Outings

Swap the boardroom for the water. A private corporate boat charter is an easy way to reward your team or entertain clients.

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Celebrations & Events

Celebrate birthdays, proposals, graduations, and bachelorette/bachelor parties with a private Chicago boat charter.

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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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Firework Cruises

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.

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Daytime Sailing

A daytime charter is an easy, unforgettable way to enjoy Lake Michigan—sunshine, skyline views, and a private boat just for your group.

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How to Book Your Chicago Boat Charter

STEP 1: Use our online booking platform (click HERE) to view available charter dates and current rates.

STEP 2: Reserve and pay directly online in under a minute.

STEP 3: After your purchase is complete, review your confirmation email for next steps on arranging a captain.

Why Book with Chicago Boat Rental?

Big selection, straightforward pricing, and captains you can trust.

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.

Gallery

Fiends posing for a group photo on the bow of a yacht with the Chicago skyline in the background.

Guest relaxing on the bow during a Chicago sunset cruise on Lake Michigan.

Portrait on the water with the Chicago skyline and Willis Tower in the background.

Yacht anchored on Lake Michigan near Chicago with guests gathered on the swim platform.

Friends posing on a boat rental in downtown Chicago with city buildings behind them.

Group photo on a Chicago boat rental with the Chicago skyline in the background.

Large party boat rental on Lake Michigan with guests swimming and relaxing on inflatable floats.

Group enjoying food and drinks inside a private charter boat during a Chicago boat rental.

Contact Us

Questions? Send us a message, call, or email.

Phone
773-236-7242

Email
info@chiboat.com