Find The Best Sailboat Rentals in Chicago.

Average of 189 reviews in this area.
12 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. NS
    Natalia
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    We had a great time with Nijole and Rimus. They were wonderful hosts and made our experience on Harmony unique and unforgettable. We admired their love of sailing and the lake and sharing that with us. We would definitely recommend taking a trip with them!

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

    Nijole and her husband were the perfect hosts. They embody professionalism, safety, and fun. Nijole knows exactly when and how to give her guests space to have fun, while also remaining present to keep her guests comfortable and safe. Most importantly, she knows how to maximize her guests' enjoyment. She gives excellent advice and offers to help her guests take pictures, party, etc. We are so glad our first experience was with such an excellent host. We can't imagine going with any one else now.

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

    🤩 WE SHOT OUR TV-SHOW on this boat 🤩- it was PERFECT. This is a REAL REVIEW - Nijole is a 5-star experience boat charter service. She is truly and authentically KIND. Encouraging and FUN! We always felt safe and secure despite our newbiesms to sailing. I would trust them with my toddler all the way up to my Great Aunt! We had such a terrific time. Please stop scrolling, stop looking, you’ve found your captain and vessel!!! If you’re still reading, here’s the best part...NO HIDDEN FEES, COSTS, SURCHARGES. What you pay through the app is what you pay. This equates to PEACE OF MIND ❤️❤️❤️ BOOK NOW 🙌🏽

  4. AD
    Andrea
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    Nijole and her husband were very kind and caring and made the experience worthwhile. Unfortunately we did have to cut our charter short due to motion sickness but they were very accommodating with helping me feel better and returning to shore. Would definitely recommend

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

    Nijola was super Responsive, kind, and fun! She was available without being in the way. We felt super comfortable to enjoy our party. And We felt safe. Great captain! I can’t wait to book more time on the water. Remember, even if you can only squeeze in 2 hours of your time it is well worth it. Don’t hesitate! Do it!

  6. JB
    Jacki
    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.