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    Captain

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,187 Reviews)

    Page 2 of 11 • 256 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    40ft Yacht w/ Huge open seating area!
    Powerboats in United States · 12 guests

    40ft Yacht w/ Huge open seating area!

    5.0
    Superowner
    Best of 2023
    $210-$240hour
    Sea Ray 38 Sundancer - Motor Yacht for Charter in Chicago, Illinois
    Events in United States · 12 guests

    Sea Ray 38 Sundancer - Motor Yacht for Charter in Chicago, Illinois

    5.0
    Superowner
    Best of 2023
    $400hour
    33' Formula Motor Yacht - Great for Playpen!
    Events in United States · 10 guests

    33' Formula Motor Yacht - Great for Playpen!

    5.0
    $150hour
    44' Luxury Sundancer Yacht Rental! Includes Floating Island!
    Events in United States · 12 guests

    44' Luxury Sundancer Yacht Rental! Includes Floating Island!

    4.8
    Superowner
    $399hour
    50' Multi-level Luxury Yacht with Party up to 12
    Events in United States · 12 guests

    50' Multi-level Luxury Yacht with Party up to 12

    5.0
    Superowner
    Best of 2023
    $350hour
    Instant Book
    42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago
    Events in United States · 11 guests

    42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

    5.0
    Superowner
    $400hour
    Private Tours on 27' Baja Boss Speedboat in Chicago with Captain Bob
    Events in United States · 5 guests

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

    5.0
    Superowner
    $200day
    Chicago Playpen and River cruises! 35’
    Powerboats in United States · 10 guests

    Chicago Playpen and River cruises! 35’

    4.9
    $295hour
    Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior
    Events in United States · 12 guests

    Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
    Sailing in United States · 3 guests

    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    4.8
    $115-$120hour
    62' $2M Italian Luxury Yacht with Party up to 12
    Events in United States · 12 guests

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

    5.0
    Superowner
    Best of 2023
    $800hour
    Instant Book
    Maxum Yacht 44' in Chicago
    Events in United States · 13 guests

    Maxum Yacht 44' in Chicago

    5.0
    Superowner
    Best of 2023
    $268-$300hour
    42FT Regal Commodore Express Cruiser
    Events in United States · 12 guests

    42FT Regal Commodore Express Cruiser

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

    33ft Day Boat in Chicago

    4.9
    $275hour
    44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
    Events in United States · 13 guests

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

    4.9
    Superowner
    $399hour
    36' Sundancer in Chicago
    Events in United States · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$250hour
    "Excelling in Excellence" Yacht Charter in Chicago, IL
    Events in United States · 13 guests

    "Excelling in Excellence" Yacht Charter in Chicago, IL

    New
    $772hour
    Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad
    Events in United States · 12 guests

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

    5.0
    Superowner
    Best of 2023
    $375-$450hour
    52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!
    Events in United States · 12 guests

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

    5.0
    Snoozed - Active 03 Feb 2025
    55' Sea Ray Luxury Yacht in Chicago
    Events in United States · 12 guests

    55' Sea Ray Luxury Yacht in Chicago

    5.0
    $325hour
    46ft Prestige Flybridge Luxury Yacht in Chicago
    Events in United States · 13 guests

    46ft Prestige Flybridge Luxury Yacht in Chicago

    4.9
    Best of 2023
    $400hour
    46' Spacious Portofino Party Yacht in Chicago For Every Occasion
    Events in United States · 12 guests

    46' Spacious Portofino Party Yacht in Chicago For Every Occasion

    5.0
    $250hour
    Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
    Powerboats in United States · 12 guests

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

    4.7
    Superowner
    $300hour
    Charter a 40' Luxury Gran Tursimo Yacht for 11 guests w/ Captain in Chicago
    Events in United States · 11 guests

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

    4.8
    Superowner
    $350hour

    Chicago Reviews

    1. Kayla

      Kayla

      50' Multi-level Luxury Yacht with Party up to 12

      After previously dealing with an unresponsive host for another listing, Edward & Team made the experience a 10/10 for us with how promptly they were able to accommodate and communicate. Communication was excellent, Captain Jim was amazing, and the boat was absolutely stunning. We had such an amazing time, and will definitely be renting this boat again in the future.

    2. Anthony

      Anthony

      Maxum Yacht 44' in Chicago

      Chris and Captain Kelly were great all around from initial booking, communication leading up to the trip, and of course the trip itself. Highly recommended for any trips in the Chicago area!

    3. 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.

    4. 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.

    5. 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!

    6. SA

      Suchi

      50' Multi-level Luxury Yacht with Party up to 12

      Celebrated my birthday on the water and watched the fireworks! A memorable trip with my friends :)

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