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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$670
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$65-$250
Fishing Charters
Let a captain do the driving while you do the fishing
$125-$250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$225
Kayaks
Who says you need a motor to have fun on the water?
$100-$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$300
TJ
Thea
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
My friends and I had such a great time on this yacht! The yacht was spacious and clean, perfect for our group to relax and enjoy the day. Everything went smoothly from booking to the very end. Kevin’s customer service was hands down the BEST I’ve experienced. He was responsive, helpful, and kept us informed every step of the way. Our captain, Evan, was just as amazing! The ride was smooth, safe, and so much fun. I highly recommend booking with Kevin, and I’ll absolutely book with him again when I return. Thanks for everything!
ED
Emma
28ft. Sea Ray Captained Boat Rental in Chicago
I can’t recommend Captain Memo enough! Not only did he go above and beyond to make my husband and I’s afternoon on his boat an awesome experience, he is also the kindest human! We had so much fun and will definitely be using him again. If you are looking for great captain, he is your guy!
VJ
Vanessa
28ft. Sea Ray Captained Boat Rental in Chicago
There’s not enough words to describe how great our experience was with Captain Memo. His communication was great. He was very knowledgeable of the water. Made our experience very memorable. If you’re looking to experience a wonderful yacht day Book now!!! Thank you Memo for going over and beyond to make sure we felt safe and have good time!!
Issam
28ft. Sea Ray Captained Boat Rental in Chicago
⭐️⭐️⭐️⭐️⭐️ We recently had the pleasure of going on a boat tour with Captain Nemo in Chicago, and we can't recommend it highly enough! From the moment we stepped aboard, Captain Nemo made us feel like family. The views of the skyline from the water were absolutely breathtaking, and the boat itself was comfortable and well-maintained. Captain Nemo's attention to detail and commitment to ensuring we had the best experience possible really stood out. Whether you’re a local or just visiting, this tour is a must-do! Thank you, Captain Nemo, for an unforgettable day on the water!
DC
Daniela
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.
Emily
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Captain Tim was amazing! He was super communicative, fun, patient, and just a great captain overall. Everybody had a great experience on the boat and absolutely loved it! The boat itself was also gorgeous. We would definitely book with Captain Tim again.
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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