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Great sailboat rentals near Chicago, Illinois.

Average of 129 reviews in this area.
15 listings

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.

GetMyBoat customer reviews for Sailing in Chicago.

  1. JS
    Jasmine
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Nijole and her husband were just amazing! Even though we were a little late, they welcomed us with enthusiasm and ensured that our time onboard was comfortable and enjoyable. Nijole took great care of us and gave us blankets and pillows to make us comfortable and keep us warm. The couple are super nice and hospitable, very warm and welcoming and made us feel like family. We were celebrating my sister’s birthday and Nijole encouraged her to take a swim in the after too, which she enjoyed immensely. Overall, I would recommend Nijole to host anyone on Harmony! Super fun experience!

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

    We highly recommend this activity. Nicole and her husband are so sweet, they were kind, and they know exactly what to do to make this unforgettable! They would serve us our own champagne, provide us with blankets even if we didn’t ask. They took 200 pictures of us with our phone, because every single moment could be an Instagram winning picture!!! We will definitely come back and send her name to family and friends!!!! Thanks!

  3. VM
    Virginia
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Nijole and her husband were absolutely fantastic! She was extremely responsive to all communication and everything went exactly as planned. We booked a trip to watch the fireworks and they got us to a perfect spot for viewing. Wonderful experience and hope to do it again soon!

  4. JP
    Jessica
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I had my bachelorette party aboard Nijole's vessel and we all had an amazing time! Nijole was very helpful in communicating with us about the weather prior to the trip, and during the trip she helped us take some fun photos around the boat. We had a great time would definitely recomend this boat and captain to everyone!

  5. RL
    REGIS
    Charter a 31' Pearson Cruising Sloop, Chicago

    This experience was amazing. Captain Joey took us to a thrilling tour around the lake ending in a beautiful sunset with a great view. The boat and Joey was a complete fun experience catered to our needs. A chill trip all around with great moments! Worth every penny. If you have a fun group, captain Joey will fit right in and make everything fun. 12/10 recommend!!

  6. MT
    Mary
    Charter a 31' Pearson Cruising Sloop, Chicago

    Had a great first sailing experience with Captain Joey! Before the outing, I was very impressed by his clear and prompt communication, especially with our concerns about the weather. We are also not from the area and he gave us clear instruction, making it easy to find him. Additionally, he was very friendly and our group very much enjoyed our sail with him and appreciated his flexibility with the timing. If we had the chance to sail in Chicago again, we would definitely call Captain Joey first!