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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$600
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$650
Sailboats
Set sail with these traditional wind-powered boats
$90-$360
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$995
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$20-$1,050
Kayaks
Who says you need a motor to have fun on the water?
$10-$425
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$375
Canoes
A classic option for leisurely paddling
$10-$25
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$130-$195
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
MR
Milena
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
My bachelorette crew and I had a phenomenal time out on the water. Weather was great, vessel was great, and we made some lifelong memories! Will definitely be back on the waters of Lake Michigan soon. An activity worth doing if you’re making a trip to Chicago.
Becca
Last Minute Playpen Clean Beautiful Boat LOA 40' Sundancer
Rented Peter’s boat for a Bachelorette party and had such a blast! Peter was wonderful to deal with and communicated and arranged everything perfectly. Our captain for the day, Alex, was awesome and made all our first time in Chicago unforgettable!! Will be back next time we are visiting the city for sure!
Raymond
Captain Memo's 28 ft. Sea Ray in Chicago
We had an Amazing time with Memo on his boat! We connected really well with our captain which I believe is really important to having a great time, the boat was very fun and Captain Memo accommodated all of our wants and needs, we will definitely be back and book with Memo again!
MS
Michael
Stylish elegance and spacious comfort ... your best time ever!
First time using this website and did not disappoint! Erika communicated everything needed ahead of time and everything from push off to returning to the dock was flawless. Would absolutely recommend Erika for your boating needs!!
DB
Dana
Captain Memo's 28 ft. Sea Ray in Chicago
We can’t recommend Captain Memo enough!! The boat was fabulous, and he had everything we could want for a celebration – speakers, cooler, under deck storage, and blowup water floats. He took photos of us throughout our adventure, and was super kind and accommodating with shifting our time slot the day of due to weather. Five stars – would sail again!
MR
Merilyn
2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024
Everything went smooth and our captain John was incredible and so sweet! Captain John always looked out for our safety especially since our experience was during the nighttime. Was helpful that he was able to provide some water and other beverages. We had an amazing experience with Nilufar’s boat!!
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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April 17, 2024
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December 30, 2019
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December 17, 2019
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August 01, 2023
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October 03, 2022
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