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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$150-$2,245
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
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$295-$360
Diving
Explore the ocean depths with trained boat operators
$125-$345
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!
M
Mark
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.
KS
Kathleen
Li'l Red, Crownline CR250 Cabin Cruiser.
Ariel was responsive and ensured we still got out and had a great day on the water, despite emergency circumstances that easily could have ruined the day. I very much recommend the experience.
DV
Danielle
Sail & Swim from a Luxury Sailing Yacht
We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!
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
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November 28, 2022
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May 20, 2021
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December 30, 2019
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December 26, 2019
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