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Fishing Charters
Let a captain do the driving while you do the fishing
$20-$150
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$150
Kayaks
Who says you need a motor to have fun on the water?
$20
Mae
28ft. Sea Ray Captained Boat Rental in Chicago
5 stars all the way! From booking our excursion to communication on the day of, Memo was great. He gave us the option of cruising down the river or spending more time at the play pen. Was so accommodating and kind. He made our day perfect!
DC
Derek
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Martin and his vessel were very well kept. The list of captains provided were very professional and polite. Martin was very prompt with communication and worked with each change needed through the process of scheduling the trip. I would very much so recommend him and his services. The trip was a success and enjoyable
SA
Shannon
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Martin's boat is great for a day on the water! It fit 12 of us comfortably. We were able to go from Belmont Harbor to the Playpen with plenty of time to swim and relax before having to head back. Also, Captain Matt and Jamie were awesome! They were looking out for both our fun and safety the whole time we were on board which was greatly appreciated.
Lynnae
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Great service great crew great experience! Michael was a very helpful and very nice deckhand! Captain Natalia was very experienced informative and thorough making sure we all made it back safe. Can’t stop hearing “3 points of contact!” in my head lol love it! Will be booking again soon.
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!
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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