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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$695
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$65-$250
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$250
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$225
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$300
Kayaks
Who says you need a motor to have fun on the water?
$110
Ashley
28ft. Sea Ray Captained Boat Rental in Chicago
Captain Memo you were awesome!! Thank you for the charter. The boat was great, you were great, the day was great! If you’re looking for a nice day out on the water with some friends/family look no further. Truly, we highly recommend using Captain Memo. Out of everyone, he was the most responsive and was an overall great person. Our group had a blast with him! Thank you again!!
Danielle
46' Luxury Yacht! Price all inclusive!
We had the absolute BEST experience with Captain Terry and Vanessa on our Lake Michigan boat charter in Chicago! From the moment we stepped aboard, we were warmly welcomed and felt completely at ease. Terry and Vanessa are not only experienced and professional, but also genuinely kind and fun people — they truly made our time on the water unforgettable. Their boat was beautiful, clean, and incredibly well-maintained. You can tell they take pride in every detail. We especially appreciated how safety-conscious they were, which made it easy for us to relax and enjoy the ride. They gave us the perfect balance of hosting and letting us do our own thing — we never felt rushed or restricted, just completely cared for and free to enjoy the experience. We had such a wonderful time cruising along the Chicago skyline and taking in the amazing views. Whether you’re celebrating something special or just looking to enjoy a peaceful and memorable day on the lake, Terry and Vanessa are the crew you want. We would absolutely book with them again and highly recommend them to anyone looking for an exceptional boat day!
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!
Daniya
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Book Kevin’s boat now! Our captain Hayden was so professional and prompt for our experience. The boat itself is gorgeous and perfect for an all girls getaway . I and my group couldn’t have asked for a better experience.
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.
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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October 03, 2022
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December 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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