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.
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.
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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.
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.
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!
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!
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.
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.