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The Best Sailboat Rentals in Illinois
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Illinois
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,000
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$5-$575
Kayaks
Who says you need a motor to have fun on the water?
$5-$270
Fishing Charters
Let a captain do the driving while you do the fishing
$5-$195
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$90-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$395
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$5-$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Top Sailboat Rental Locations Near Illinois
Recent Reviews in Illinois
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.
Rachel
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was incredibly helpful, communicative, and kind. She was responsive and went above and beyond to help us reschedule when bad weather struck. We had a lovely trip and she and her husband were delightful to be around! I highly recommend their boat and I can’t wait to sail with them again sometime.
SS
Sam
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
I can’t begin to express how kind and courteous our hosts were. They made our trip incredible from the time we stepped on the boat until the time we departed. My friends and I all felt that they went above and beyond to make our experience memorable. If you are looking for a good time on the water look no further and book right here!
GR
Gayle
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
We had SUCH a good time on Nijole's boat! We did a sunset/fireworks cruise and it was just the absolute best time, could not recommend it more highly. We were all talking about renting again with Nijole (and her husband and pup Piper) as soon as we got off!
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
Real reviews from happy Getmyboaters.
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