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    Find The Best Sailboat Rentals in Chicago.

    Average of 389 reviews in this area.
    11 listings
    37' Luxury Sailboat with Captain
    hour$275
    Super Owner6 guests

    37' Luxury Sailboat with Captain

    Charter a 31' Pearson Cruising Sloop, Chicago
    hour$150
    Super Owner6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    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

    38' Catalina Sailing Cruise in Chicago
    hour$250
    6 guests

    38' Catalina Sailing Cruise in Chicago

    Learn Kiteboarding in Chicago, Illinois
    hour$120
    1 guest

    Learn Kiteboarding in Chicago, Illinois

    Step onboard a sailboat for an unforgettable experience in Chicago, Illinois.

    Get ready for a fun adventure when you hit the open water onboard a sailboat in Chicago, Illinois. Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Chicago, Illinois is a wonderful sailboat rental destination.

    Using GetMyBoat to rent your next sailboat.

    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.

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    GetMyBoat customer reviews for Sailing in Chicago.

    1. KH
      Kirsten
      37' Luxury Sailboat with Captain

      This was an amazing way to spend the morning on the water. Greg was obviously a great sailor and able to handle his 37' boat by himself. He was full of knowledge about the area and we loved hearing all the fun facts about the city of Chicago.

    2. GM
      Gerald
      37' Luxury Sailboat with Captain

      We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

    3. MC
      Michael
      Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

      Everything was perfect! Nichole was very warm and friendly and a great capitan! The boat easily accomodated our group of five, we had perfect weather and really enjoyed our three hour sail (which seemed too go by in the blink of an eye). Love sailing in Chicago!

    4. ML
      Minyan
      Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois

      Wonderful sailing experience! Captain Mike was very helpful and professional during the whole trip. My friends and I have already decided that we will try this again next summer!

    5. 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.

    6. Gabriel
      Gabriel
      37' Luxury Sailboat with Captain

      Great experience, would highly recommend. Was greated at arrival, Greg was an amazing host. The whole experience was perfect for our group. From departure to arrival I would happily do it again.