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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$205-$1,115
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$990
Sailboats
Set sail with these traditional wind-powered boats
$180-$450
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$600-$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
Kayaks
Who says you need a motor to have fun on the water?
$120
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275
DM
Derrick
Captained charter on 40' Sea Ray with all amenities in Chicago!
Spacious boat with great sound system . Had a great time ln this vessel . Crew and captain were nice and very accommodating .
EM
Esteban
Relax And Enjoy This Beautiful Carver Yacht
Definitely would book again! It was perfect and we all enjoyed it!
EW
Eunice
Sea Ray Express Cruiser 340 Luxury Motor Yacht in Chicagoland
We had an amazing time! There's nothing like being on the water and we can't wait to do it again! We got stuck in the rain for about 20min but Captain Tia and the crew were so professional and calm, we knew we were in good hands. It didn't put a damper on things at all! They made it easy to stay positive and keep the party going once things cleared up.
jaida
Rent the Maxum 3000 SCR Motor Yacht in Lake Michigan, Chicago
My friends and I had an amazing time on Vance’s boat! This is my second time renting his boat, and it’s always a pleasure. He is very responsive on the app, and created a great experience for us. He was also very understanding for a late comer in our group. Vance brought us to playpen in Chicago quickly and safely for the black charter weekend. I would highly recommend booking with Vance!
LT
Lena
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
We rented two boats from Captain James for a big group birthday celebration and it was so much fun! He was quick to respond and always answered any questions we had. We were able to sail and dock together, everything was easy and seamless. Everyone had a wonderful time!
Brittany
50' Sea Ray Sundancer Yacht for 13 Guests in Chicago, IL -Reduced Price! (MPY#1)
We rented the yacht for our friend’s 30th birthday bash and had an amazing time! Everyone associated with the boat, along with our captain, was so helpful and nice. We could not have asked for a better experience! Make sure to bring some ice for the cooler along with you. And know that there is an opportunity to get into the lake and swim if you’d like!
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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November 23, 2022
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October 03, 2022
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April 14, 2022
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December 11, 2020
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December 29, 2019
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