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Page 7 of 10 • 240 listings
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Washington
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David
39' SeaRay Sundancer for 11 Guests – 3 Boats! Weekday Discount!
Capt John and his boats/deckhands/captains are all great! Very easy to communicate with and get all the insights you want. We had 2 families with 5 kids overall and it was a great trip. We booked on Chicago Scene day and we were able to see some of the fun, but we also stayed further away from the main playpen. Capt had to dock up once to let off some family members early on the trip and it was seamless. The Sundancer is in great condition and a lot of fun to be on. Highly recommend.

Reymond
'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!
We had an incredible July 4th charter with Danyelle! Her crew was extremely professional and made sure our group of 12—celebrating a pre-wedding event—was well taken care of. The trip included a beautiful skyline tour followed by relaxing time at the Playpen, with stunning views all around. The photos came out amazing too. Highly recommend and would absolutely book again!

Bianca
'Genius' 40' Sea Ray Sundancer Captained Charter with all amenities in Chicago!
Danyelle and her crew ( James & Davion ) gave me the best 24th birthday I could ask for. They were very attentive and showed us the best time while also keeping us safe. We didn't want our charter to end. They showed us a tour of the city and took us to play pen. I couldn't have asked for a better experience!!! We will definitely be doing another trip with them. 10/10 recommend.
KW
Kierra
41' Stunning Sea Ray Yacht - Stunning throughout
Mr Bennett boat was beautiful! He’s very communicative, very kind, and welcoming. The entire process from booking to trip end was seamless. The boat was very clean and spacious. I hosted a summer celebration, my friends and I and had an amazing time! I will only be booking with Norman going forward! 🎉

Jahkayah
Chicago Private Boat Rental - Explore Chicago's Skyline and Waters - SUCESSION
What a fantastic experience! I rented Alex's boat yesterday and had an absolute blast with my group of 12 friends. From the moment we arrived, Alex was super friendly and welcoming. He showed us around the boat and made sure we felt comfortable and at ease. The boat itself was immaculate - clean, well-maintained, and organized to perfection. Alex had thought of everything to ensure our day on the water was stress-free and enjoyable. His assistant was also super helpful in getting us settled and answering any questions we had. Alex himself was an absolute pleasure to be around. He was knowledgeable about the area and gave us great recommendations for things to do and see. His enthusiasm was infectious, and he really made us feel like we were part of his own little crew. We had an amazing time cruising around the water, taking in the sights, and enjoying each other's company. The boat handled beautifully, and we were able to fit all 12 of us comfortably. Overall, I would highly recommend renting from Alex. His attention to detail, warm hospitality, and love for boating make for a truly unforgettable experience. We can't wait to come back and do it again!
JR
Jose
53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
Couldn't recommend Peter, his Captain Dean, and this boat more. This was a 10/10 experience. The boat was clean (even though it came back from another charter 30 minutes before), comfortable inside and out, large bathroom, great sound system, large lily pad, and the full-size fridge was great for storage. I look forward to booking this boat again and recommend that you do too!