Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio
3–6 hrs
Up to 13 people
Kitchen, 2 bathrooms, sound system
Set out aboard a 50-foot Sea Ray Sundancer with space for food, drinks, and music. Relax on deck and use the onboard kitchen, bathrooms, refrigerator, and coolers.
This booking is for the whole experience, which fits up to 13 guests.
No refund for cancellations 6 days or less before departure. Receive an 85% refund when cancelling 14 days before departure or a full refund one month before. Weather-related cancellations are not refunded, but you may postpone. Receive a full refund if the operator cancels for reasons they are responsible for.
Product ID: JTEMTV
No. Gratuity is not included in the listed price. A 20% tip is standard, optional, and welcome.
Bring your own food, ice, drinks, and liquor. Leave shoes, cigarettes, and cigars ashore.
Special-event rate increases apply for events including Memorial Day, the Air & Water Show, Chicago Scene Party, Independence Day, and Labor Day.
Chicago-based luxury yacht charter with a near-perfect track record across dozens of celebrations, from birthdays and bachelorette parties to corporate outings. The concierge team, particularly Gia and Ben, consistently earns praise for thorough communication, smooth coordination, and making sure every detail is handled before you even step on board. The captains are a genuine highlight here. David, Ken, Bill, Mike, and Bishop all get called out by name in reviews, which says a lot about the personal experience you can expect on the water. Guests frequently mention feeling safe, comfortable, and genuinely looked after throughout their trip. The boats themselves are described as well-maintained and nicely equipped, with water toys adding a fun bonus for the right crowd. Several reviewers also noted with pride that this is a Black-owned business, which clearly resonates with a meaningful portion of their clientele. For anyone planning a group event in Chicago, this outfit covers a lot of ground: the Playpen, river cruises, sightseeing, and private charters all get mentioned. Hard to find much to complain about in the feedback, and the repeat booking intentions speak for themselves.
Me and my girlfriends had an amazing time on our charter with Captain Mike this past Saturday! Not only was the boat gorgeous but he provided us with a Lilly pad, let us play our music as loud as we wanted, and made sure we had an amazing (and safe) time. First time at the playpen and won’t be the last!
Erin Kelly
August 10, 2026
Me and my girlfriends had an amazing time on our charter with Captain Mike this past Saturday! Not only was the boat gorgeous but he provided us with a Lilly pad, let us play our music as loud as we wanted, and made sure we had an amazing (and safe) time. First time at the playpen and won’t be the last!
Erin Kelly
August 10, 2026
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