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    Incredible sailboat rentals in Illinois, United States.

    Average of 396 reviews in this area.
    15 listings
    37' Luxury Sailboat with Captain
    hour$300
    Super Owner6 guests

    37' Luxury Sailboat with Captain

    Charter a 31' Pearson Cruising Sloop, Chicago
    hour$200
    Super Owner6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    "Class Action" Hunter Legend
    hour$321
    Super Owner6 guests

    "Class Action" Hunter Legend

    Bareboat Sailing Catamaran in Chicago, Illinois
    hour$650
    13 guests

    Bareboat Sailing Catamaran in Chicago, Illinois

    38' Cruising Catamaran Charter in Chicago, Illinois
    hour$600
    12 guests

    38' Cruising Catamaran Charter in Chicago, Illinois

    38' Gemini Sailing Catamaran in Chicago, Illinois
    hour$550
    6 guests

    38' Gemini Sailing Catamaran in Chicago, Illinois

    Catalina 380 Sailing Monohull in Chicago, Illinois
    hour$275
    7 guests

    Catalina 380 Sailing Monohull in Chicago, Illinois

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

    38' Catalina Sailing Cruise in Chicago

    Set Sail in Downtown Chicago
    hour$250
    6 guests

    Set Sail in Downtown Chicago

    Learn Kiteboarding in Chicago, Illinois
    hour$120
    1 guest

    Learn Kiteboarding in Chicago, Illinois

    Your Friend With A Boat
    hour$250
    10 guests

    Your Friend With A Boat

    Boating Guide - Illinois Sailing

    Rent or charter a sailboat for a memorable experience in Illinois.

    Are you ready for a fun adventure out on the open water onboard a sailboat in 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. Illinois is a wonderful sailboat rental destination.

    Using GetMyBoat to book your next sailing experience.

    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 Sailing in Illinois.

    1. Rusty
      Rusty
      37' Luxury Sailboat with Captain

      A really pleasant day on a really nice boat with a highly capable captain

    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. Bailey
      Bailey
      37' Luxury Sailboat with Captain

      We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.

    4. Dyna
      Dyna
      37' Luxury Sailboat with Captain

      I rented the boat to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner! The boat is very spacious! We had 6 people and Greg was our captain but still had so much space to move around the boat! Greg is very laid back and easy to talk to. We brought food, alcohol and birthday cupcakes on board the boat. There’s a mini fridge to keep stuff cold. There was an aux cable so I was able to play music. There’s also a bathroom on the boat. Overall, I’d definitely recommend Greg and Cait!

    5. SM
      Scott
      37' Luxury Sailboat with Captain

      Greg was a patient, sure captain who did a great job showing us around the lake. He knew weather was going to roll in before it actually did and made sure we got in our fun and got us to the dock right before a storm rolled through and was kind enough to allow us to stay aboard until it was done. Great job

    6. BB
      Brandon
      37' Luxury Sailboat with Captain

      It was an amazing relaxing time , fully stop. Nothing but good conversation with my party and the captain and his first mate. Everything was clean and they were great host. Even help ppl in my party that got motion sickness. They are clearly experts at sea and hosting. Book this boat and make memory.

    GetMyBoat has 15 listings for Sailing experiences in Illinois with 396 reviews.

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