Find The Best Sailboat Rentals in Chicago.

Average of 92 reviews in this area.
7 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.

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GetMyBoat customer reviews for Sailing in Chicago.

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

    We had a wonderful time sailing with Nijole and her husband Remus (I probably spelled that wrong, apologies!). Lake Michigan and views of Chicago are stunning, we had perfect weather, and the boat and her crew were wonderful. Highly recommended, especially as a somewhat "physically distanced" option in these times.

  2. ND
    Charter a 31' Pearson Cruising Sloop, Chicago

    We had a wonderful time with Captain Joey! The weather was perfect for cruising around and sailing. The Captain showed us beautiful views of the city skyline and there was never a dull moment on board. I would definitely book again with Captain Joey and recommend others to do so too.

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

    Nijole and her husband are hands down the best you will find in chicago! Every aspect of this reservation has been a pleasure and delight. Highly recommend!! Will use them again!

  4. am
    Charter a 31' Pearson Cruising Sloop, Chicago

    Captain Joey was so great! Friendly and full of knowledge about sailing. We were celebrating a birthday and it was just perfect! Highly reccomend..harbor is Easy to access and beautiful views!

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

    Absolutely lovely. It was such a nice boat with a perfect captain. Both Nijole and Remus were expert sailors and friendly and kind. Excellent trip!

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

    What a lovely ride! Nijole was very kind and enjoyable for the entire ride. Would love to sail with her again in the future!