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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$60-$695
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$800
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$470
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$35-$560
Sailboats
Set sail with these traditional wind-powered boats
$75-$505
Kayaks
Who says you need a motor to have fun on the water?
$10-$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$375
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$125-$500
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$60-$80
Canoes
A classic option for leisurely paddling
$65
DV
Danielle
Sail & Swim from a Luxury Sailing Yacht
We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!
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!
AI
ANTHONY
Beautiful Yacht 40 LOA 340 Sundancer Searay
Peter is the best. Communication 100, patience- 100 out of 100. He is the best among the rest. I will recommend Peter 100 x out of 100. Look no more, you gat the best among the rest.... thank you Capitano ...
Lilian
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
I had such a great time with my friends! The captain was very kind and the ride was smooth sailing! Definitely book with Kevin!
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!
August 24, 2023
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April 17, 2024
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April 17, 2024
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October 09, 2023
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December 30, 2019
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August 01, 2023
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