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Page 2 of 15 • 353 listings
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Thad
44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
It was a pleasure — better than advertised and my friends and I had a great time out there!! Would recommend and rent from Jimmy again

Julia
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Definitely recommend booking with Jason. The booking process and communication leading up to our reservation was top notch. My group had an amazing time and the boat was beautiful! Captain Jimmy was also great and made sure we were taken care of. Looking forward to booking with Jason again in the future.
JY
Jordan
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Jason and Justin did a great job communicating and coordinating our trip. We did 3 hours and then the rain affected our time so we added another hour. Justin was a fun captain and helped us have the best time possible. We definitely recommend renting Jason’s yacht and having Justin as your captain. Will be back for the next season of boating!
KJ
Kaylan
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
We had an amazing time on Jason’s boat celebrating a 30th birthday! Our captain Justin was phenomenal. Everything was just as it was on the listing. Boat was clean, as was the bathroom. Ice and coolers were provided as well as kitchen utensils. An amazing deal comparatively. Wouldn’t change a thing! Thank you Jason and Justin!
MM
Melanie
Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Jason has very competitive pricing that is well worth it. Communication was very easy. He provided me with a very simple list to find a captain (which was the piece I was most worried about). The boat came with ice and cups which made it so easy for hosting. Had a great time!
HG
Hardik
26 ft. Chaparral SSX257 Luxury Vessel
I rented this boat for the weekend to propose to my girlfriend, with the stunning backdrop of the Navy Pier and Chicago skyline — and the entire experience was absolutely perfect. From the start, the process was seamless and professional. Mark was incredibly responsive and helpful, answering all of my questions quickly and thoroughly. Communication was smooth throughout, and the boat itself was exactly as described — clean, well-maintained, and just like the listing photos. A special shout-out to our captain, Eduard, who went above and beyond to help with planning and flawlessly executing the proposal. He was not only professional and accommodating, but also a genuinely great person to spend time with. This experience exceeded all expectations, and I couldn’t have asked for a better setup for such a memorable moment.