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
$175-$870
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$5-$570
Kayaks
Who says you need a motor to have fun on the water?
$5-$415
Fishing Charters
Let a captain do the driving while you do the fishing
$5-$195
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$95-$805
Sailboats
Set sail with these traditional wind-powered boats
$125-$370
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$5-$150
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$395
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$350-$750
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!
mm
maira
Captain Memo's 28 ft. Sea Ray in Chicago
An overall wonderful experience! Communication was great with the captain from the start as he guided us through the phone to find the boat, the boat itself was clean with excellent service from the Bluetooth speaker to the cooler with ice; It was a Saturday night so witnessing the fireworks on the water is definitely a 10/10, my toddler very much enjoyed it as well! Thank you captain Memo 😊
TH
Tory
Captain Memo's 28 ft. Sea Ray in Chicago
Memo was a great captain! We appreciated his communication immediately upon booking all the way through our reservation. Throughout our trip, he made sure the experience was exactly what we wanted. Would definitely recommend him to anyone looking for the ideal Chicago boating experience.
KC
Kaylee
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
We had the absolute BEST time with Captain Kevin, Captain Steve, and Skipper Manny for my bachelorette party! Even despite the choppy water, they made sure to keep us safe AND have a great time. I wish I could give them 6 stars. 10/10 recommend!!
MR
Milena
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
My bachelorette crew and I had a phenomenal time out on the water. Weather was great, vessel was great, and we made some lifelong memories! Will definitely be back on the waters of Lake Michigan soon. An activity worth doing if you’re making a trip to Chicago.
Becca
Last Minute Playpen Clean Beautiful Boat LOA 40' Sundancer
Rented Peter’s boat for a Bachelorette party and had such a blast! Peter was wonderful to deal with and communicated and arranged everything perfectly. Our captain for the day, Alex, was awesome and made all our first time in Chicago unforgettable!! Will be back next time we are visiting the city for sure!
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!
April 17, 2024
Read Article
August 24, 2023
Read Article
May 03, 2023
Read Article
October 11, 2021
Read Article
March 27, 2020
Read Article
August 01, 2023
Read Article
Boat Rentals
the United States
Illinois