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    Captain
    All listings in Chicago

    Search yacht rentals in Chicago, Illinois.

    4.8
    (3,019 Reviews)

    Page 2 of 10 • 217 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago
    Events in Chicago · 11 guests

    42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

    5.0
    Superowner
    $400hour
    44' Luxury Sundancer Yacht Rental! Includes Floating Island!
    Events in Chicago · 12 guests

    44' Luxury Sundancer Yacht Rental! Includes Floating Island!

    4.8
    Superowner
    $399hour
    42FT Regal Commodore Express Cruiser
    Events in Chicago · 12 guests

    42FT Regal Commodore Express Cruiser

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
    Powerboats in Chicago · 12 guests

    Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

    4.7
    Superowner
    $300hour
    62' $2M Italian Luxury Yacht with Party up to 12
    Events in Chicago · 12 guests

    62' $2M Italian Luxury Yacht with Party up to 12

    5.0
    Superowner
    Best of 2023
    $800hour
    Instant Book
    Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior
    Events in Chicago · 12 guests

    Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    33ft Day Boat in Chicago
    Events in Chicago · 10 guests

    33ft Day Boat in Chicago

    4.9
    $275hour
    Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad
    Events in Chicago · 12 guests

    Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad

    5.0
    Superowner
    Best of 2023
    $375-$450hour
    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
    Events in Chicago · 5 guests

    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

    5.0
    Superowner
    $200day
    "Excelling in Excellence" Yacht Charter in Chicago, IL
    Events in Chicago · 13 guests

    "Excelling in Excellence" Yacht Charter in Chicago, IL

    New
    $772hour
    36' Sundancer in Chicago
    Events in Chicago · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$250hour
    55' Sea Ray Luxury Yacht in Chicago
    Events in Chicago · 12 guests

    55' Sea Ray Luxury Yacht in Chicago

    5.0
    $325hour
    52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!
    Events in Chicago · 12 guests

    52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!

    5.0
    $250hour
    46ft Prestige Flybridge Luxury Yacht in Chicago
    Events in Chicago · 13 guests

    46ft Prestige Flybridge Luxury Yacht in Chicago

    4.9
    Best of 2023
    $400hour
    44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
    Events in Chicago · 13 guests

    44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

    4.9
    Superowner
    $399hour
    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL
    Events in Chicago · 6 guests

    2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

    5.0
    $500hour
    Luxurious 60' Yacht with Fly Bridge
    Events in Chicago · 12 guests

    Luxurious 60' Yacht with Fly Bridge

    5.0
    $450hour
    46' Spacious Portofino Party Yacht in Chicago For Every Occasion
    Events in Chicago · 12 guests

    46' Spacious Portofino Party Yacht in Chicago For Every Occasion

    5.0
    $250hour
    Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago
    Events in Chicago · 11 guests

    Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago

    4.8
    Superowner
    $350hour
    40ft Boat w/ HUGE open seating area!
    Events in Chicago · 12 guests

    40ft Boat w/ HUGE open seating area!

    5.0
    Superowner
    Best of 2023
    $210-$240hour
    **Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**
    Events in Chicago · 12 guests

    **Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**

    5.0
    Superowner
    Best of 2023
    $250hour
    Amazing Party Trips on 34ft Cruiser in Chicago
    Events in Chicago · 16 guests

    Amazing Party Trips on 34ft Cruiser in Chicago

    4.9
    Superowner
    $425hour
    NEW!!! SPACIOUS 40ft Cruisers Yacht, Power…in the Lake, Chicago
    Events in Chicago · 12 guests

    NEW!!! SPACIOUS 40ft Cruisers Yacht, Power…in the Lake, Chicago

    5.0
    Superowner
    $400hour
    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

    5.0
    Superowner
    Best of 2023
    $250hour

    Motor Yacht Reviews in Chicago

    1. Victor

      Victor

      36' Sundancer in Chicago

      Excellent captain and very knowledgeable and friendly. We had a great time and conversed on many interesting topics related to Chicago and the lake. I definitely recommend him.

    2. PK

      Pavel

      Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob

      The trip was awesome. The boat is great and powerful, Robert knows a lot about Chicago. Absolutely recommended.

    3. Kaitlin

      Kaitlin

      44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

      Highly recommend! Jimmy was very nice and he even rescheduled us to the following day due to bad weather. He made my birthday very special and I would definitely book with him again in the future!

    4. Yunyi

      Yunyi

      42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

      John and his crew really made us feel home. Communication was always quick and in time. The boat was easy to find and clean and well equipped. Our party had little children and seniors so Captain Derroll and his crew were extra attentive to them. They were very accommodating when some of us got sea sick. We had a great experience and would highly recommend anybody choosing experience!

    5. DP

      Daniel

      42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

      Absolutely fantastic trip. Captain John and his team were really easy to work with and the day went very smoothly. Everyone was really friendly and the boat was perfect for our group. Massive thankyou again and we will certainly be looking to rebook a trip in the near future.

    6. AA

      Alyssa

      42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

      John was so easy to work with. Always responded quickly and was informative on the process. His crew was super helpful and always made sure we were having fun. Daryl was a great captain, made sure we had drinks filled, drove the boat perfectly and gave us a great spot to jump in the water. The boat was exactly as described and was the perfect boat for our group of 10 girls. Perfect amount of space as well as shaded area in the boat and on the second floor when you needed a break from the sun. Would definitely recommend this rental to anyone and will definitely be using John’s boat in the future!

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