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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$925
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$45-$655
Fishing Charters
Let a captain do the driving while you do the fishing
$15-$660
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$570
Kayaks
Who says you need a motor to have fun on the water?
$5-$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$375
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$15-$760
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$15-$195
Canoes
A classic option for leisurely paddling
$10-$15
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
AD
Alejandro
Charter a 31' Pearson Cruising Sloop, Chicago
Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.
AC
Alicia
37' Luxury Sailing Yacht in Downtown Chicago
When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!
Andrew
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Our group had a great time! I would recommend using Nicole for your sailing trip!
Federica
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
I was so happy to do this experience but I didn’t know that I was going to like it so much ! I would recommend having this boat for a 2 date or double date ! The owners are really lovely but the best part is going to the pope and sitting there ! Make sure you bring wine, glassware and whatever you want to have ! 2 hours was a perfect time for us! Us we were lucky enough to have of the best sunsets of the season !
vp
vadim
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
I want to thank Nijole for her work . Everything was perfectly organized, swimming and sailing. My daughter got seasick and we received full support from the captain. There was also a miracle dog on board ! Dog swam with us and gave us a good mood! Thank you very much! If you want to have a wonderful time sailing, then you are definitely to Nijole! With respect, Vadim Pliss!
AL
Adam
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
We loved our experience with Nijole. They took us all around the lake and we loved every minute of it. We even got to swim! They are also a very fun time to hang out with and enjoy the day. Definitely recommend and we will be booking with them multiple times this boating season.
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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October 09, 2023
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August 24, 2023
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December 30, 2019
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August 01, 2023
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