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Sailboats
Set sail with these traditional wind-powered boats
$75-$175
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$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
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$145
Beatris
Ultimate 52 " Yacht at Diversey Harbor –Perfect for PlayPen!
My experience booking with Jason was a 10/10 through and through from beginning to end. The entire process was seamless, from booking the boat rental to the actual boat day. Jason provided great communication and answered all of my questions promptly. The boat itself was even better than I imagined, very beautiful with a lot of space, very clean and well kept. The captain that was recommended was a great time and really took care of us. I thoroughly enjoyed my entire experience and will be booking with him again!
CR
Celine
Diversey Harbor Relax and Enjoy on this 52ft Yacht
Kevin did an amazing job of making sure we had a positive experience. He called to let us know that there would be a change in of time and captain and made that process seamless. Anytime I’m in Chicago I will be sure to reach out for a rental!
Paul
Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!
Great time! Only advice is to get your captain booked early! So ask them for a list. Cost of $500 is in your fee but need book Captain directly. Tip is usually 20%. Captain Mike was the best!! Trip was a great time for family and friends. Thank you!!!!
TJ
Thea
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
My friends and I had such a great time on this yacht! The yacht was spacious and clean, perfect for our group to relax and enjoy the day. Everything went smoothly from booking to the very end. Kevin’s customer service was hands down the BEST I’ve experienced. He was responsive, helpful, and kept us informed every step of the way. Our captain, Evan, was just as amazing! The ride was smooth, safe, and so much fun. I highly recommend booking with Kevin, and I’ll absolutely book with him again when I return. Thanks for everything!
ED
Emma
28ft. Sea Ray Captained Boat Rental in Chicago
I can’t recommend Captain Memo enough! Not only did he go above and beyond to make my husband and I’s afternoon on his boat an awesome experience, he is also the kindest human! We had so much fun and will definitely be using him again. If you are looking for great captain, he is your guy!
VJ
Vanessa
28ft. Sea Ray Captained Boat Rental in Chicago
There’s not enough words to describe how great our experience was with Captain Memo. His communication was great. He was very knowledgeable of the water. Made our experience very memorable. If you’re looking to experience a wonderful yacht day Book now!!! Thank you Memo for going over and beyond to make sure we felt safe and have good time!!
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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