We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$115-$1,540
Sailboats
Set sail with these traditional wind-powered boats
$110-$675
Fishing Charters
Let a captain do the driving while you do the fishing
$85-$660
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$75-$750
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$665
Kayaks
Who says you need a motor to have fun on the water?
$40-$1,845
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$160-$1,725
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$80-$275
Whale Watching
See some of the ocean’s most incredible creatures with these eco tours
$365-$2,150
Diving
Explore the ocean depths with trained boat operators
$125-$345
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$295-$360
Canoes
A classic option for leisurely paddling
$30
Sandra
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Capt. Tim and crew were very accommodating and helpful. We rented the boat to scatter a loved ones ashes close to Navy Pier. Capt Tim was very receptive to our feelings and knew actually what we needed. We had a great celebration of life on his boat!
EL
Erika
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was easy to coordinate with, got back to me quickly, and the boat was just as pictured. Captain Justin was accommodating and personable. Couldn’t have asked for a better day on the boat! We’ll definitely be coming back!
PD
Prina
28ft. Sea Ray Captained Boat Rental in Chicago
Our party of 4 had a great time on Captain Memo’s boat. He was very communicative and sent a helpful video on where to find the marina. He also took pictures for us and sent them promptly following the ride. He made us feel very safe and welcomed.
Annette
SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
Beautiful large boat for a bachelorette, plenty of seating space, we were able to hire a masseuse that provided massages in one of the rooms since it was a bit chilly, which was convenient. Will def rent again!
GK
Guy
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
We had an amazing day out on the boat. Jason was very helpful in the build up and Captain Jimmy was brilliant! The boat s huge and perfect for a trip on the lake. We would 100% do this again! So much fun.
NR
Natalia
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Kevin was awesome, super communicative, friendly, and made sure we were taken care of. There was a change to our departure time and a delay afterward, but he kept us well informed throughout. Captain Justin and his deckhand were fantastic hosts, making the experience fun and relaxing. We celebrated my husband’s birthday and had an absolute blast, even with the chilly May weather in Chicago. Overall, a great experience and highly recommend!
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 01, 2023
Read Article
October 03, 2022
Read Article
December 11, 2019
Read Article
August 24, 2023
Read Article
April 10, 2020
Read Article
December 30, 2019
Read Article