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Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$45-$575
Sailboats
Set sail with these traditional wind-powered boats
$125-$435
Fishing Charters
Let a captain do the driving while you do the fishing
$20-$200
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
$100-$395
Kayaks
Who says you need a motor to have fun on the water?
$15-$80
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$40-$100
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275-$750
AB
Andy
70' EXCLUSIVE Motor Yacht NEW to Chicago
We’ve chartered 10+ boats in Chicago over the years and nothing compared to the experience we just had with Fun in the Sun! Thank you for the hospitality, timeliness, and professionalism. I will recommend friends & family and will definitely be booking with Damian again! Thank you.
JR
James
Last Minute Memorial Day Deal $200/Hour on a 40' Luxury Yacht
This charter was amazing from the beginning to the end! Captain G responded right away & answered all my questions. The communication was great! The boat beautiful, clean & spacious. The surround sound system was the best ever! We danced and sang with Captain TJ who was so fun. Ww really appreciate Captain TJ who was available to be our captain. We'll definitely book with Captain G again! This was by far the funnest activity we did this Memorial Day weekend!
CF
Carson
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
I cannot recommend LTD Charters enough! LTD has very timely responses, making the process of arranging the trip seamless. The boat ride itself was fantastic and LTD was super accommodative. Captain Z, Captain Kevin, and Kate were so helpful on board and made sure we had the best time! The boat had everything we needed and was better than we could have expected! Book with LTD for your next trip!
Veronica
32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Thank you for the exceptional service! We instantly felt welcomed and taken care of! We had the best time and couldn’t ask for a better captain and co captain! We will be booking again! Thank you habibi!
Allyssa
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Kevin was great! The boat was even better than the pictures and him and the crew were so kind and inviting! He communicated with me efficiently and made the experience so smooth. We had an amazing time for my friend’s bachelorette and couldn’t recommend Kevin enough! 😊
Ruthwik Sai
2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024
Absolutely thrilled with our experience on this private yacht! From start to finish, the host and captain were exemplary, making us feel warmly welcomed and ensuring seamless communication throughout. The yacht itself was impeccably maintained, offering everything we needed for a truly memorable voyage. Highly recommend for anyone seeking a top-tier experience on the water!
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 24, 2023
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April 17, 2024
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May 03, 2023
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October 11, 2021
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March 27, 2020
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August 01, 2023
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