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Page 2 of 12 • 279 listings
Ravid
38-ft Party Pontoon for Up to 20 Guests in Chicago
My friends and I had an amazing time on Captain Greg's boat! The boat had speakers, cooler, a bathroom, floaties, pretty much everything we needed. The boat was very spacious and comfortable. The crew were very friendly and welcoming as well! We had so much fun sailing around Chicago and swimming in the lake, it was a perfect boating experience!
NV
Natalie
25ft Rinker - Captained included in price- Chicago
Highly recommend Joe and his boat! He made my birthday so special. The boat is equipped with everything you may need - ice and a cooler. And of course, all the toys for the water. The views were spectacular and he recommended doing a cruise before anchoring and getting in the water which we loved. The speaker is also so nice to listen to your favorite tunes!!
LV
Louie Chelle
42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!
We had an amazing time on Captain John's yacht! The boat was very nice, spacious, and exactly as described. It was perfect for a group of girls celebrating a college reunion! Captain John helped coordinate and get us set up right before takeoff, then we had Captain Dee and Hussein with us for the ride. They were all great and courteous! FYI - you will need to reach out to their list of captains to confirm (this was told to us the week of), but honestly, it sounded like they made sure someone was available regardless, so likely a formality. Definitely would book again for future Chicago trips!
MS
Michael
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
I had some friends visiting Chicago and wanted to impress them. Renting a boat from Kevin was the crown jewel of the weekend! Our captain Evan was very professional, accommodating and friendly. The boat exceeded expectation. Would definitely book with them again!
ED
Elena
40' Luxury Cruiser Yacht for Charter in Chicago
We had the BEST time aboard Captain G’s boat thanks to Captain TJ & Deckhand Eric!!! Such a perfect sized boat for 12 people with awesome speakers & storage. Captain TJ was so fun and took some amazing photos/videos while we thoroughly enjoyed the playpen! Can’t wait to book them again next summer and would 11/10 recommend!!! 🙌⛵️❤️
JO
Jessica
My friends and I plan a summer boat day every year. I got in contact with Chris who was very responsive from the start and very helpful through the entire booking. We reached out to captain Dan Chavez and I was so happy that we did. He made the experience amazing and was very attentive throughout our time. He prioritized our safety and had gave us a great time. Would mostly highly recommend for an amazing time!