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Fishing Charters
Let a captain do the driving while you do the fishing
$40-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$40-$200
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$200-$400
Kayaks
Who says you need a motor to have fun on the water?
$25-$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$140-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110
Sailboats
Set sail with these traditional wind-powered boats
$325
CB
Colin
27' Sea Ray Sundancer – Extended Swim Platform
Alex and his brother did an excellent job making it a very fun and relaxing boating experience for my friend's bachelor party. We all had a great time and would definitely want to do it again, plus would highly recommend to anyone else looking to experience Chicago Boat Scene
Rb
Raven
44' Luxury Sundancer Yacht Rental! Includes Floating Island!
Had an amazing time on our boat charter! From start to finish, everything was smooth, professional, and beyond enjoyable. The crew was friendly, knowledgeable, and made sure we felt safe and relaxed the whole time. The boat itself was spotless and well-equipped, with everything we needed for a fun day on the water. Whether we were cruising, sunbathing, or dropping anchor to swim, it was an unforgettable experience. Highly recommend to anyone looking to escape, unwind, and enjoy a perfect day at sea!
KP
Kendra
Hunter 43 Sailing Yacht in Oakville, Ontario
We had a great time on Dave’s boat! He recommended a beach area where we could anchor and swim around and let the kids get involved with the sailing when they asked. Very friendly and the boat was exactly what we expected.
cf
carolynn
Sail & Swim from a Luxury Sailing Yacht
This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)
SQ
Safiya
27' Sea Ray Sundancer – Extended Swim Platform
Our charter cancelled at the last minute and Alex came in like a super hero and saved the day! We had a phenomenal time aboard his boat. He’s very friendly and accommodating. I will definitely recommend.
TC
Tami
44' Sea Ray Express Luxury Motor Yacht Rental in Chicago
If you want a great boat and a great time book this boat! Captain Alex was amazing and fun and we will be booking this again. BOOK THIS BOAT - FYI it is on 31st harbor just so you know
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!