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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$180-$940
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$5-$585
Kayaks
Who says you need a motor to have fun on the water?
$5-$410
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$800
Sailboats
Set sail with these traditional wind-powered boats
$125-$370
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$395
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$5-$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
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Alexa
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Had an amazing day on the water during the Air and Boat Show with Captain Bob as our guide. He's helpful in giving instructions to the dock, helps set up music and ensures a comfortable and safe experience. Due to his background in the CFD, he knew exactly where to anchor the boat so we could see great views of the air show. It was a worthwhile and memorable experience to share with friends and family!
Carlos
17ft Fishing boat Rental
Very accommodating, given the time we booked was rained out luckily were able to push our outing longer, clean boat great people would 10/10 be booking again in the future thank you Yurri and wife!
Grace
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Bob was a fantastic captain, making our tour of Chicago and the Playpen unforgettable. His knowledge and friendliness ensured we had a great time. 12/10 would go again!!
VT
Vivien
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Captain Bob was just overall awesome. Enough said.
MK
Megan
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
Captain Bob is professional, very knowledgeable of the city, entertaining, and made our experience super enjoyable!
EB
Elizabeth
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
Earl was an absolute pleasure to work with- very flexible and gave us the chance to have the best day in his boat! The boat is large and spacious and we had a wonderful time
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
April 17, 2024
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August 24, 2023
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May 03, 2023
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October 11, 2021
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March 27, 2020
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September 13, 2023
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