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Page 10 of 10 • 240 listings
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RM
Ross
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
Amazing experience from booking until we finally docked after our adventure. Captain Matt, and the deckhand Joe were extremely professional, cool, and accommodating. The boat was better than expected. It was large, very clean, and it had an exceptional sound system, which was easily connected to Bluetooth. I would 100% book again with this boat.
SE
Sabrine
50' Multi-level Luxury Yacht with Party up to 12
So stunning, and a TON of fun! You get a little tour of Chi and a ton of pic opportunities and then a good amount of time to swim or paddle board. So amazing and definitely will book again!
CB
Colin
27' Sea Ray Sundancer – Luxury Cruise with Extended Swim Platform
Alex and his brother did an excellent job making it a very fun and relaxing boating experience for my friend's bachelor party. We all had a great time and would definitely want to do it again, plus would highly recommend to anyone else looking to experience Chicago Boat Scene
AB
Amanda
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
We had the most amazing girls' weekend, and we can't rave enough about our experience! Armand, Captain Matt, and Deckhand Joe were absolutely wonderful to work with. They went above and beyond to make sure everything was perfect for us—from the moment we stepped on the boat until the very end. The boat itself was beautiful, clean, and so comfortable—perfect for relaxing, soaking in the sun, and having a great time on the water. But what truly made the weekend unforgettable was the incredible crew. Captain Matt was professional, friendly, and made us feel safe and at ease the entire time. Deckhand Joe was equally fantastic—helpful, fun, and always making sure we had everything we needed. We’re so grateful for everything they did to make our weekend special. Highly recommend this experience if you're looking for the perfect mix of relaxation, fun, and top-notch service on the water!
JG
Jack
Burnham Harbor, CAPTAIN/FUEL INCLUDED
We had an unforgettable experience with Captain Joe and deckhand Ryan! They were incredibly accommodating and flexible, adjusting our itinerary to work around storms so we could still make the most of the day. Their professionalism and positive energy made the entire trip a blast—we were celebrating my 30th birthday, and it couldn’t have been better. The float tube was a huge hit and added so much fun to our time on the water. Highly recommend booking with them—would absolutely do it again!
SG
Stephanie
Special End of Season Sunday pricing for 8 to 13 passengers
My friends and I rented Captain Russell’s boat for a wedding weekend celebration and had the best time! The boat was beautiful, and Captain Brian made the whole experience super enjoyable. Highly recommend!