We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,000
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$710
Sailboats
Set sail with these traditional wind-powered boats
$120-$370
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$600-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150-$180
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$200
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
Kayaks
Who says you need a motor to have fun on the water?
$50-$120
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65
jaida
Yachting on 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!
EW
Eunice
SeaRay Express Cruiser 340 Luxury Motor Yacht Searay in Chicagoland area
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.
KM
Karlie
50' Sea Ray-12 Passengers *BELIEVE CHICAGO*
This could not have been a better experience booking with Captain Carlos! We had a group of 20 girls for a bachelorette and booked two of his boats to take out and tie up together. His team was professional and ensured we had an amazing time. The boats we rented were clean, spacious, and had awesome speaker systems. Definitely the highlight of our weekend!
Sandra
50' Sea Ray-12 Passengers *BELIEVE CHICAGO*
I would highly recommend booking with Captain Carlos. He made the experience stress-free by being great about communicating. The boat is absolutely beautiful and had more than enough room to accommodate all 11 of us. We hired Captain Moni as the driver of the boat and he brought along Lala as a deckhand. Both were SO sweet, personable and made the whole experience that much better. I would recommend this team to anyone booking a boat in Chicago.
Kelly
50' Sea Ray-12 Passengers *BELIEVE CHICAGO*
Captain Carlos and his team were absolutely wonderful! Captain Mike cancelled on us 2 weeks out (and never bothered to text us and let us know) so we ended up scambling 5 days before our event without a captain. Captain Carlos and his team went above and beyond to make sure we didn't need to cancel our event, and ensured we had a fabulous time!
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!
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
Read Article
November 23, 2022
Read Article
October 03, 2022
Read Article
April 14, 2022
Read Article
December 11, 2020
Read Article
December 29, 2019
Read Article