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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$990
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$45-$660
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
MC
Mary
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Our experience on this charter was top notch for my friend's bachelorette party! We worked with Captain Kevin to coordinate the day and he made everything so easy and replied to all of our questions super fast (like within minutes). The crew was very friendly and asked us about our preferences for cruising versus docking throughout the trip. They took us to all the best stops and made the whole experience priceless. Thank you!!!
MD
Mel
Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
Tamer is amazing! Thanks so much for being not just our captain, but also an amazing tour guide. He was very accommodating. He gave us snacks and drinks and made sure we saw all of Chicago. He got along with everyone and made sure we were all comfortable.
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
$250/Hour Daily on a 40' Cruiser 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!
AA
Ayomide
27' Chris Craft with Water Toys plus Jet Ski Available
10/10 customer service! Capt. Tim was amazing! From getting us on the boat to helping us get amazing photos with the chicago skyline and the buckingham fountain in the background. We will definitely be back for the bigger boat again. Thank you!!!
rm
rachel
27' Chris Craft with Water Toys plus Jet Ski Available
We rode with Tim over MDW and he was seriously the best. The boat was amazing and easily fit me and my 5 friends, he was accommodating, friendly, and personable. I would chose Tim over and over!!! 1000/10 recommend!!! We had the best time 🤍🛥️
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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August 24, 2023
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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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Boat Rentals
the United States
Illinois