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    Find The Best Sailboat Rentals in Chicago.

    Average of 515 reviews in this area.
    1 - 18 of 22 listings
    37' Luxury Sailboat with Captain
    hour$300
    Super Owner6 guests

    37' Luxury Sailboat with Captain

    Private Cruise onboard Hunter Legend Sailboat in Chicago
    hour$200
    Super Owner6 guests

    Private Cruise onboard Hunter Legend Sailboat in Chicago

    Charter a 31' Pearson Cruising Sloop, Chicago
    hour$200
    Super Owner6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    38' Sailing Catamaran, Chicago's Largest!
    hour$500
    Super Owner12 guests

    38' Sailing Catamaran, Chicago's Largest!

    Set Sail in Downtown Chicago
    hour$250
    Super Owner6 guests

    Set Sail in Downtown Chicago

    Super Spacious Silverton Express Cruiser in Chicago, Illinois
    hour$350
    Super Owner12 guests

    Super Spacious Silverton Express Cruiser in Chicago, Illinois

    "Class Action" Hunter Legend
    hour$321
    Super Owner6 guests

    "Class Action" Hunter Legend

    38' Gemini Sailing Catamaran in Chicago, Illinois
    hour$450
    6 guests

    38' Gemini Sailing Catamaran in Chicago, Illinois

    43' Tiara Motor Yacht Rental in Chicago, Illinois
    hour$550
    12 guests

    43' Tiara Motor Yacht Rental in Chicago, Illinois

    410 Sundancer Motor Yacht Rental in Chicago, Illinois
    hour$500
    12 guests

    410 Sundancer Motor Yacht Rental in Chicago, Illinois

    Catalina 380 Sailing Monohull in Chicago, Illinois
    hour$275
    7 guests

    Catalina 380 Sailing Monohull in Chicago, Illinois

    22 results

    GetMyBoat customer reviews for Sailing in Chicago.

    1. YH
      Yousuf
      Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

      Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!

    2. SS
      Sam
      Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

      I can’t begin to express how kind and courteous our hosts were. They made our trip incredible from the time we stepped on the boat until the time we departed. My friends and I all felt that they went above and beyond to make our experience memorable. If you are looking for a good time on the water look no further and book right here!

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

      We had SUCH a good time on Nijole's boat! We did a sunset/fireworks cruise and it was just the absolute best time, could not recommend it more highly. We were all talking about renting again with Nijole (and her husband and pup Piper) as soon as we got off!

    4. DB
      Diana
      Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

      Nijole was awesome! We were greeted by her and her adorable pup (Piper) to tour the Lake/playpen area. She was incredibly friendly and had my sisters and I laughing. She was very accommodating as well. The excursion was more relaxing than anything.

    5. Sara
      Sara
      37' Luxury Sailboat with Captain

      My fiancé and I planned a engagement photoshoot, however, due to weather conditions not cooperating, Greg was so flexible at rescheduling with us. He made us feel very comfortable and gave tips on how to take the most beautiful photoshoot out of the beautiful scenery of the city. Would totally recommend him! By the way, the boat was spotless, so clean and so so beautiful😍

    6. ML
      Mary
      Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois

      Look no further for a sail tour! Michael is an amazing sailing captain and has so many great stories. There was equal time to chat along with serene, idyllic moments during our time on the water. A perfect balance...incredible from start to finish!

    Boating Guide - Chicago Sailing

    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 has 22 listings for Sailing experiences in Chicago with 515 reviews.

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