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Sailboats
Set sail with these traditional wind-powered boats
$120-$1,000
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$130-$1,000
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$200
Kayaks
Who says you need a motor to have fun on the water?
$15-$80
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$380
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$200
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$1,000
RB
Richard
Family Fun! 20ft Avalon Tritoon – 150HP | Double Bimini | Tow Bar | 1Hr minimum
Super fun time . Shane was a great captain . I would totally do it again and recommend to anyone that just wants to enjoy the water without having to worry about anything . I got to wakeboard and just enjoy the river. Good Times !!
Sandra
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Capt. Tim and crew were very accommodating and helpful. We rented the boat to scatter a loved ones ashes close to Navy Pier. Capt Tim was very receptive to our feelings and knew actually what we needed. We had a great celebration of life on his boat!
Corey
Family Fun! 20ft Avalon Tritoon – 150HP | Double Bimini | Tow Bar | 1Hr minimum
Jennifer was awesome during the booking process. Very communicative and answered all the stuff. Captain Shane reached out right away and thru the process. Was early to the dock, and we had a blast. Very knowledgeable of the River and all her history. Was truly like going on a boat with your buddy. We will 100% book again next time. Thanks Shane, and thanks Jennifer.
Daniya
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Book Kevin’s boat now! Our captain Hayden was so professional and prompt for our experience. The boat itself is gorgeous and perfect for an all girls getaway . I and my group couldn’t have asked for a better experience.
EL
Erika
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was easy to coordinate with, got back to me quickly, and the boat was just as pictured. Captain Justin was accommodating and personable. Couldn’t have asked for a better day on the boat! We’ll definitely be coming back!
MO
Melissa
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
My group of 12 had a blast! I usually rent a boat yearly and I must admit, this was my FAVORITE boating experience thus far! We will definitely be using Kevin D again! Thank you for a great 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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December 30, 2019
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August 01, 2023
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October 09, 2023
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December 12, 2019
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November 23, 2022
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