Private 37-Foot Yacht Charter in Chicago
Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing
From$1,550
Search all experiences
Discover what we've curated for you
Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing
Discover what we've curated for you
3–4 hrs
Up to 13 people
Private yacht, Bluetooth audio
Board a well-equipped 37-foot Rinker Fiesta Vee and enjoy a BYOB cruise on Lake Michigan or the Chicago River. Plan your own itinerary and relax with family or friends during a flexible three- or four-hour charter.
USCG regulations limit charters to 12 passengers; infants and children count toward this total. Children 13 and under must wear life jackets, and only service animals with life jackets are permitted on board. Red wine, staining items, glass containers, feathered boas, glitter, confetti, drugs, weapons, and open flames are prohibited.
Cancellation requests incur a 5% non-refundable fee. Cancel 14 or more days in advance for a full refund minus the fee, 4–13 days prior for a 50% refund minus the fee, and within 3 days for no refund. If weather is deemed unsafe, you may postpone or reschedule within one year.
31st Street Harbor on J Dock
Knot My Boat Charters has clearly figured out the formula for creating memorable lake experiences. The standout feature here is the impressive roster of captains who consistently deliver exceptional service. John Brown gets multiple shout-outs for being friendly, informative, and creating a relaxed vibe that lets groups truly enjoy themselves. Captain Brian earns high marks not just for his professionalism and safety focus, but for going above and beyond (one reviewer mentioned how he secured a forgotten bag and coordinated its return after hours). Captain Rudy and Captain Josh also receive praise for being accommodating and laid-back, giving groups the freedom to customize their trips. The booking process gets thumbs up for being seamless and straightforward, with the nice perk of choosing your captain upfront. Reviewers consistently mention bringing their own snacks, playlists, and comfort items like blankets and hoodies, which suggests this is a BYOB-style charter where you control the atmosphere. Groups have used the service for everything from bachelor parties to Northwestern game day excursions, with stops at popular spots like "the playpen." The company also helps coordinate catering if needed. With such consistently glowing feedback about the captains' personalities, boat quality, and overall experience, this looks like a solid choice for anyone wanting a fun, stress-free day on the water without unnecessary frills or complications.
I went out with Knot My Boat Charters this past August with some friends and had such a great experience. From the moment we booked, everything was simple and easy. The staff onboard were so friendly, professional, and really easy to talk to. They were helpful the entire time and made sure we were comfortable and having a good time. It was also a beautiful day out on the water, which made the experience even better. Overall, it was such a fun and memorable day. I’d definitely recommend Knot My Boat Charters to groups of friends, family get-togethers, or even corporate events. I would absolutely book with them again!
Jackie Guesneau
March 2, 2026
I went out with Knot My Boat Charters this past August with some friends and had such a great experience. From the moment we booked, everything was simple and easy. The staff onboard were so friendly, professional, and really easy to talk to. They were helpful the entire time and made sure we were comfortable and having a good time. It was also a beautiful day out on the water, which made the experience even better. Overall, it was such a fun and memorable day. I’d definitely recommend Knot My Boat Charters to groups of friends, family get-togethers, or even corporate events. I would absolutely book with them again!
Jackie Guesneau
March 2, 2026