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    Windy City Sailing

    4.9 (12 reviews)
    Closed 9:00 am - 5:00 pm

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    Services - Windy City Sailing

    Boat charters

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    4 years ago

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    6 years ago

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    11 years ago

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    15 years ago

    Yare vessels and as salty a crew as you'll find in fresh water. A real Chicago experience.

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    9 years ago

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    8 years ago

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    Ask the Community - Windy City Sailing

    Review Highlights - Windy City Sailing

    Edwina was amazing to work with on logistics in advance of our sail and Captain Marty and crew were so accommodating the day of!

    Mentioned in 4 reviews

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    Chicago Land Yacht Rental - Beautiful Chicago sunset

    Chicago Land Yacht Rental

    (9 reviews)

    Lakeview

    I recently rented a yacht from this company for my birthday, and the experience exceeded all…read moreexpectations :) From the moment we boarded, the captain was professional, welcoming and very attentive to all of our requests. The yacht itself was super clean, beautifully maintained, and equipped with everything we needed --plenty of space, float rafts to hang out on, great sound system, and perfect views from the top of the yacht. The captain was amazing--knowledgeable, friendly, and made us feel safe and relaxed. He has DECADES of experience and knows the lake Michigan and the Chicago river like the back of his hand. We cruised along stunning views of the Chicago skyline, and we saw the sunset on the way back. It was pure magic and oh so romantic. Perfect for a cancer horoscope sign such as myself;) I highly recommend this yacht rental company for anyone looking to celebrate, relax, or just enjoy an amazing Chicago experience on the water. I will be booking again!!

    Chicagoland Yacht Rentals completely ruined what should have been one of the happiest days of our…read morelives. We rented a yacht for a gender reveal celebration, and what we experienced was traumatizing, unsafe, and felt like a complete setup. The captain, Joe, seemed fine at first he even helped us open our biodegradable powder cannons and posed for pictures. But seconds after the reveal, he started yelling that he needed to "settle everyone down" and demanded I Zelle him $400 on the spot for him to start while claiming the boat was damaged. He blamed his "friend," who then came aboard and aggressively insulted our entire family yelling in front of all our guests and young children. Two children were so traumatized!! This celebration turned into fear and panic. It didn't end there. The captain was drinking alcohol, slurring his words, smoking, and taking unauthorized photos of minors. His behavior was reckless and disturbing. We have video proof of his conduct. When I contacted Chicagoland Yacht Rentals, they did absolutely nothing. No call, no check-in, no apology just silence and a ridiculous claim that I had "spray painted the boat." I'm eight months pregnant, and they want to blame me for something I physically couldn't have done. We're now out thousands, and I've had to file a police report and begin legal proceedings. This company is dangerous, dishonest, and completely unprofessional. The dozens of 5-star reviews seem fake they don't match what we went through. Please do not trust them with your money, your event, or your family's safety.

    Windy City Sailing - boatcharters - Updated May 2026

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