GetMyBoat Logo

    Top rated cruising catamaran rentals near Chicago, Illinois.

    Average of 25 reviews in this area.
    3 listings
    Bareboat Sailing Catamaran in Chicago, Illinois
    hour$650
    13 guests

    Bareboat Sailing Catamaran in Chicago, Illinois

    38' Cruising Catamaran Charter in Chicago, Illinois
    hour$500
    13 guests

    38' Cruising Catamaran Charter in Chicago, Illinois

    40' Gemini Sailing Catamaran in Chicago, Illinois
    hour$450
    6 guests

    40' Gemini Sailing Catamaran in Chicago, Illinois

    Grab your camera and step aboard a cruising catamaran in Chicago, Illinois.

    Looking for a relaxed cruising experience on your next trip to Chicago, Illinois? Cruising catamaran rentals and charters are a great way to explore by boat for a day, bringing your friends and family onboard. Catamarans offer ample space to spread out and enjoy on-board activities, or you can stop for a relaxing swim during your boat ride. A cruising catamaran is the perfect choice for a special event or during a vacation that you want to spend on the water, and for touring a new area. Cruising catamarans are a great style of boat to explore Chicago, Illinois in comfort.

    Using GetMyBoat to rent your next cruising catamaran.

    Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

    Search for the perfect experience now and book your dream day out on the water.

    GetMyBoat customer reviews for Cruising Catamaran in Chicago.

    1. Josh
      Josh
      Bareboat Sailing Catamaran in Chicago, Illinois

      My friends and I have chartered a few boats here in Chicago, but this was by far the best experience we have had. We actually had to reschedule our initial cruise last minute due to bad weather. The boat owner, Russel, was very communicative and made the best of the not-so-great situation. He graciously offered to allow for our group to enjoy the boat for a lesser amount of time and stay at the dock. We were also able to reschedule for the following week and go out with Captain Brian at that time. Our group had such an amazing time during both sessions. We certainly had some strong personalities in the bunch (myself included) and Captain Brian was such a great sport. He was very professional but also blended in so well with our group that he was like another guest. We will without a doubt be reaching out to Russel & Captain Brian again for future events. Thank you both for making this such an unforgettable experience for us and our guests.

    2. ND
      Nicole
      Bareboat Sailing Catamaran in Chicago, Illinois

      Captain Brian was so helpful when some of our group experienced sea sickness. He was super fun to be around and made the trip so great!

    3. Aimee
      Aimee
      38' Cruising Catamaran Charter in Chicago, Illinois

      Beautiful boat, sailing was magical! Plenty of space for our party of 10. Loved relaxing on the trampoline out front. Captain and crew were friendly and so helpful. Can’t wait to go back again!

    4. SD
      Shaunak
      38' Cruising Catamaran Charter in Chicago, Illinois

      Captain Brian and Russell were A W E S O M E!!! From the beginning, Brian was great ... very responsive to inquiries and follow up questions. During the cruise, that's when our experience went from GREAT to AWESOME! Brian and Russell were great, on-time, professional and courteous. They took good care of us and just let us relax. Thank you for making our UChicago graduation celebration weekend a fun and memorable experience! HIGHLY RECOMMEND cruising the lakefront and swimming in the Play Pen!!

    5. Veronica
      Veronica
      38' Cruising Catamaran Charter in Chicago, Illinois

      My friends and I rented the catamaran boat from Jim for the 4th of July and had such an amazing time. The boat was even better in person and comfortably fit me and 12 of my friends. Captains Russell and Brian were also amazing. They were so much fun and so accommodating. They set everything up for us (the cooler with all of our drinks, bowls of chips we had brought, etc). We rented the boat for 3 hours but were having such a good time that we asked if we could pay to extend our use for another hour. Luckily they had no other immediate obligations and they were able to make it happen. As a nice bonus, they even had those fun water noodles for us to use. So much fun and my friends and I can't wait for our next boat outing with these guys!

    6. Julia
      Julia
      Bareboat Sailing Catamaran in Chicago, Illinois

      We had such a great time. The boat was better in person, and Captain Brian was awesome. I highly recommend him and 1st Class Charters (Chicago). Definitely worth it all around.