Incredible sailboat rentals in Illinois, United States.

Average of 404 reviews in this area.
12 listings
37' Luxury Sailboat with Captain
hour$275
Lake MichiganCruising Monohull
Super Owner6 guests

37' Luxury Sailboat with Captain

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
hour$180
Lake MichiganCruising Monohull
Super Owner6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

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

Charter a 31' Pearson Cruising Sloop, Chicago

Private Cruise onboard Hunter Legend Sailboat in Chicago
hour$200
Lake MichiganCruising Monohull
6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

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

Bareboat Sailing Catamaran in Chicago, Illinois

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

38' Cruising Catamaran Charter in Chicago, Illinois

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
hour$80
Lake MichiganBeach Monohulls
3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

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

40' Gemini Sailing Catamaran in Chicago, Illinois

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

38' Catalina Sailing Cruise in Chicago

Learn Kiteboarding in Chicago, Illinois
hour$120
Lake MichiganNon Powered Watercraft
1 guest

Learn Kiteboarding in Chicago, Illinois

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. 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. KH
    Kimberly
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!

  5. JH
    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. BB
    BRIAN
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    Wonderful trip to honor my father who passed away, and who loved sailing on Lake Michigan in the 1950s on his small sailboat. The boat was just large enough to accommodate the 3 of us, which was perfect - a large vessel or motorboat would not have been pertinent to my father's history. Ben was easy to talk to and understood the importance of what we were doing, which made it all the better. Unforgettable trip.