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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$205-$1,110
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$80-$790
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$95-$800
Sailboats
Set sail with these traditional wind-powered boats
$180-$450
Fishing Charters
Let a captain do the driving while you do the fishing
$20-$340
Kayaks
Who says you need a motor to have fun on the water?
$10-$250
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$300
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275
BM
Bridget
38-ft Party Pontoon for Up to 20 Guests in Chicago
We had an incredible experience. We booked for a co-ed bachelorette party. The captain and other staff on board were SO friendly and accommodating. The cooler was plenty big, the bathroom was clean, and we had a nice space to set up our sandwiches. Great experience!
DM
Derrick
Captained charter on 40' Sea Ray with all amenities in Chicago!
Spacious boat with great sound system . Had a great time ln this vessel . Crew and captain were nice and very accommodating .
KA
King
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Great experience!! Nice boat!! Will definitely book again.
AG
Abby
Stunning 45’ Sea Ray Yacht
Beautiful yacht! Captain Peter was awesome and very accommodating.
JA
Jennifer
Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
Excellent service!!!
MP
Molly
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
We rented Kevin’s boat for my bachelorette party. Communication leading up to and day-of was great. He even provided a video to show where we should park. We had a different captain and skipper for the day and both were wonderful. We could tell that they took our safety seriously. The weather made the water very choppy, and we were told we shouldn’t go to the usual “play pen” area bc of this. They took us out a little ways where we could still get nice views of the city and have our own space on the water. They also provided coolers and other items for us to make drink and food storage and service easy. I would absolutely recommend this to anyone wanting to have a great boating experience. My friends and I left saying we should do it every year.
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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October 11, 2021
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March 27, 2020
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August 01, 2023
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Boat Rentals
the United States
Illinois