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Boat Rentals
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the United States
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Illinois
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Winthrop Harbor
Sailboats
Set sail with these traditional wind-powered boats
$75-$175
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$145
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175
Kayaks
Who says you need a motor to have fun on the water?
$50
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$145
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!
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.
KA
Kelly
27 ft Sea Ray, Captain Included
Bobby was the best captain! We left right on time and the water was beautiful. He had a cooler with ice prepared and ready for us upon arrival, and made the whole trip a time to remember! I could not recommend him enough!
TC
Tom
Manitou 23ft Pontoon on the Milwaukee River
Ryan provided an excellent tour of the Milwaukee river. He’s very personable and informative and my crew thoroughly enjoyed themselves. I highly recommend him as a captain, we will definitely hire him the next time we’re in town.
CM
Cynthia
28ft. Sea Ray Captained Boat Rental in Chicago
Captain M was great!! On time, had us laughing and very personable! Boat was perfect for a relaxing day on the lake with a group of 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 01, 2023
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November 23, 2022
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October 03, 2022
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April 14, 2022
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December 11, 2020
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December 29, 2019
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Boat Rentals
the United States
Illinois
Winthrop Harbor