We use cookies to improve your browsing experience.
And dolphins make us happy. Find out more about our cookies policy here.
Sailboats
Set sail with these traditional wind-powered boats
$120-$440
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$775
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$120-$800
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$75-$200
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$75
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$185
KH
Kyle
Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
I've had the pleasure of renting this boat for my birthday celebrations two years in a row, and each experience has been nothing short of fantastic! The boat is in impeccable condition, clean, and well-maintained, making for a comfortable and enjoyable ride on the water. The captain and crew are incredibly professional, friendly, and accommodating. They go above and beyond to ensure that every guest has a memorable experience. The captain's knowledge of the local waters is impressive, and they always find the best spots for swimming. The boat itself is spacious and well-equipped, with ample seating, a great sound system, and all the necessary safety equipment. Whether you're looking to relax and soak up the sun or enjoy some water sports, this boat has everything you need for a perfect day on the water. I can't recommend this boat enough for anyone looking to celebrate a special occasion or simply enjoy a day out on the water. I'm already looking forward to booking it again for my next birthday!
Kayla
50' Multi-level Luxury Yacht with Party up to 12
After previously dealing with an unresponsive host for another listing, Edward & Team made the experience a 10/10 for us with how promptly they were able to accommodate and communicate. Communication was excellent, Captain Jim was amazing, and the boat was absolutely stunning. We had such an amazing time, and will definitely be renting this boat again in the future.
Anthony
Maxum Yacht 44' in Chicago
Chris and Captain Kelly were great all around from initial booking, communication leading up to the trip, and of course the trip itself. Highly recommended for any trips in the Chicago area!
PK
Pavel
Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
The trip was awesome. The boat is great and powerful, Robert knows a lot about Chicago. Absolutely recommended.
Kaitlin
44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
Highly recommend! Jimmy was very nice and he even rescheduled us to the following day due to bad weather. He made my birthday very special and I would definitely book with him again in the future!
SA
Suchi
50' Multi-level Luxury Yacht with Party up to 12
Celebrated my birthday on the water and watched the fireworks! A memorable trip with my friends :)
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 24, 2023
Read Article
December 16, 2019
Read Article
April 17, 2024
Read Article
May 03, 2023
Read Article
October 11, 2021
Read Article
March 27, 2020
Read Article