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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$775
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$620
Sailboats
Set sail with these traditional wind-powered boats
$100-$360
Kayaks
Who says you need a motor to have fun on the water?
$10-$435
Fishing Charters
Let a captain do the driving while you do the fishing
$70-$1,065
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$70-$1,130
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$40-$375
Canoes
A classic option for leisurely paddling
$10-$25
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$130-$195
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
JY
Jordan
Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat
Jason and Justin did a great job communicating and coordinating our trip. We did 3 hours and then the rain affected our time so we added another hour. Justin was a fun captain and helped us have the best time possible. We definitely recommend renting Jason’s yacht and having Justin as your captain. Will be back for the next season of boating!
Adam
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Had an incredible time out on Kevin’s boat. We had Captain Justin and I couldn’t recommend him enough. We were celebrating a bachelor party and this was the highlight of the weekend!
RG
Ravi
Captain Memo's 28 ft. Sea Ray in Chicago
An awesome experience - right from booking the trip, the trip itself, and the warmth and responsiveness of Capt Memo. The boat was awesome - clean and with space up front and in the back of the boat. Capt Memo asked us upfront how we wanted to spend our time and ensured we got exactly what we wanted. He also took some great pictures which he shared promptly. And he engaged with us when we welcomed it but also gave us space when we wanted it. All in all, we loved the experience and will certainly be back
FN
Francis
70' EXCLUSIVE Motor Yacht NEW to Chicago
Damian and Monica (and Jimmy) were a pleasure as captain, staff, and assisting with our trip. Everything was on time and their initial instructions were easy to understand and friendly. Our trip included both the the river and lake and was a beautiful day. Our originally scheduled Saturday had bad weather forecasted and we were lucky enough to reschedule for the day after. This was a surprise for my Mom and when the boat arrived it was huge, clean and ready to go. We brought our own food, drinks, and also had the ability to play our own music. The boat was the biggest on the water and we loved the multiple locations on the boat to hang out to eat and drink. It was an unforgettable day and I would not hesitate to use them again. I highly recommend it!
MM
Melanie
Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat
Jason has very competitive pricing that is well worth it. Communication was very easy. He provided me with a very simple list to find a captain (which was the piece I was most worried about). The boat came with ice and cups which made it so easy for hosting. Had a great time!
KJ
Kaylan
Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat
We had an amazing time on Jason’s boat celebrating a 30th birthday! Our captain Justin was phenomenal. Everything was just as it was on the listing. Boat was clean, as was the bathroom. Ice and coolers were provided as well as kitchen utensils. An amazing deal comparatively. Wouldn’t change a thing! Thank you Jason and Justin!
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!
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