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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,140
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$90-$950
Fishing Charters
Let a captain do the driving while you do the fishing
$30-$340
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$800
Sailboats
Set sail with these traditional wind-powered boats
$125-$535
Kayaks
Who says you need a motor to have fun on the water?
$10-$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$350
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$300
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275-$800
JS
Jessica
46' Spacious Portofino Party Yacht in Chicago For Every Occasion
We had such a great time! Kyle was great to work with and very responsive making the whole process easy. Captain G was awesome as well and really helped make the experience fun and smooth. We’ll definitely be booking the boat again! Highly recommend!
PD
Prina
28ft. Sea Ray Captained Boat Rental in Chicago
Our party of 4 had a great time on Captain Memo’s boat. He was very communicative and sent a helpful video on where to find the marina. He also took pictures for us and sent them promptly following the ride. He made us feel very safe and welcomed.
GK
Guy
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
We had an amazing day out on the boat. Jason was very helpful in the build up and Captain Jimmy was brilliant! The boat s huge and perfect for a trip on the lake. We would 100% do this again! So much fun.
PP
Priscilla
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Booked the boat for my family and friends and had a BLAST! We still talk about how fun it was. The captain was easy to book and everything went super smoothly from booking to the actual event. Will be booking again this year !!
NR
Natalia
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was awesome, super communicative, friendly, and made sure we were taken care of. There was a change to our departure time and a delay afterward, but he kept us well informed throughout. Captain Justin and his deckhand were fantastic hosts, making the experience fun and relaxing. We celebrated my husband’s birthday and had an absolute blast, even with the chilly May weather in Chicago. Overall, a great experience and highly recommend!
NK
Nitin
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
Had an amazing time on the yacht! Jason was super responsive and made planning really easy. Captain Kevin was great — everything was smooth, on time, and well-coordinated. They really helped us just enjoy the moment. Would definitely recommend this boat to friends!
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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August 01, 2023
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Boat Rentals
the United States
Illinois