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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$45-$700
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$770
Fishing Charters
Let a captain do the driving while you do the fishing
$40-$505
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$55-$725
Sailboats
Set sail with these traditional wind-powered boats
$90-$450
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$375
Kayaks
Who says you need a motor to have fun on the water?
$15-$275
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$60-$130
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$120-$275
Canoes
A classic option for leisurely paddling
$65
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 .
AG
Abby
Stunning 45’ Sea Ray Yacht
Beautiful yacht! Captain Peter was awesome and very accommodating.
MP
Molly
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
We rented Kevin’s boat for my bachelorette party. Communication leading up to and day-of was great. He even provided a video to show where we should park. We had a different captain and skipper for the day and both were wonderful. We could tell that they took our safety seriously. The weather made the water very choppy, and we were told we shouldn’t go to the usual “play pen” area bc of this. They took us out a little ways where we could still get nice views of the city and have our own space on the water. They also provided coolers and other items for us to make drink and food storage and service easy. I would absolutely recommend this to anyone wanting to have a great boating experience. My friends and I left saying we should do it every year.
MF
Maddie
Stunning 45’ Sea Ray Yacht
We rented out this yacht for my boyfriend’s birthday party! The boat was spacious and just as described. Our captain Peter and his wife were an amazing crew, thorough with safety, attentive, and went above and beyond to make sure that we had an incredible time! Booking with Eugene was a breeze, he was quick to respond, as well as answered every question that I asked! Everyone had a blast, and we will definitely be booking through them again!
Bianca
Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago
Danyelle and her crew ( James & Davion ) gave me the best 24th birthday I could ask for. They were very attentive and showed us the best time while also keeping us safe. We didn't want our charter to end. They showed us a tour of the city and took us to play pen. I couldn't have asked for a better experience!!! We will definitely be doing another trip with them. 10/10 recommend.
Mardysa
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
I had an amazing time! I booked on rather short notice and Kevin came through for me especially with helping to find a captain for such a busy day. The entire process was smooth and Captain Lisa was great! I’d definitely book with him again in the future.
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!