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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$270-$465
Sailboats
Set sail with these traditional wind-powered boats
$75-$150
Fishing Charters
Let a captain do the driving while you do the fishing
$150-$300
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150-$300
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$150
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maira
Captain Memo's 28 ft. Sea Ray in Chicago
An overall wonderful experience! Communication was great with the captain from the start as he guided us through the phone to find the boat, the boat itself was clean with excellent service from the Bluetooth speaker to the cooler with ice; It was a Saturday night so witnessing the fireworks on the water is definitely a 10/10, my toddler very much enjoyed it as well! Thank you captain Memo 😊
TH
Tory
Captain Memo's 28 ft. Sea Ray in Chicago
Memo was a great captain! We appreciated his communication immediately upon booking all the way through our reservation. Throughout our trip, he made sure the experience was exactly what we wanted. Would definitely recommend him to anyone looking for the ideal Chicago boating experience.
KC
Kaylee
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
We had the absolute BEST time with Captain Kevin, Captain Steve, and Skipper Manny for my bachelorette party! Even despite the choppy water, they made sure to keep us safe AND have a great time. I wish I could give them 6 stars. 10/10 recommend!!
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.
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!
CC
Claire
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
I chartered Jason's incredible boat with Captain James (Jimmy) for my 26th birthday with 12 friends (13 total) & it was an incredible day! The boat was exactly as described, we played our music on the Bluetooth speaker, swam with the lilypad provided, enjoyed the ice & coolers provided, and had the best day! Jason & Jimmy were incredibly responsive & I had the best chartering experience yet with them. Would highly recommend chartering with them!
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 01, 2023
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October 03, 2022
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December 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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