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Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$170-$1,035
Sailboats
Set sail with these traditional wind-powered boats
$125-$535
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$200-$800
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$350
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$130-$195
Kayaks
Who says you need a motor to have fun on the water?
$120
Bria
Beautiful Yacht 40 LOA 340 Sundancer Searay
Our group of 11 had an amazing time out on the lake with captain pete! He communicated well and had all of the amenities needed- coolers, Lilly pad, blue tooth, refrigerator space for food, etc. the boat was clean and had lots of space, accurate to listing. We would definitely book with Captian Pete again!
OT
Olivia
Stunning 45’ Sea Ray Yacht
Fantastic Experience with Peter and Team! Peter was incredible—he even met us in the parking lot with a wagon to help transport our drinks and food. He was extremely friendly and communicative from start to finish. My coworkers and I had an amazing time cruising around the lake. The only minor downside was needing to bring our own ice, but everything else was absolutely 10/10. We’ll definitely be booking with Peter and his team again!
Mark
Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
Ali was EXCEPTIONAL with the logistics, and Captain Z was AWESOME with the boating!!! We had group of five, and the accommodations fit our group exceptionally well. Our only regret is that the four hours went by so fast! lol! Highly recommend, and will DEFINITELY keep him in mind for the next excursion!
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!
Shannon
'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!
This was our second year in a row booking this boat. They have consistently delivered the best customer service. I have been renting yachts for years and this is the only boat to provide ice and water making the experience very comfortable. I couldn’t recommend them enough!
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!
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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December 16, 2019
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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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