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    03/30/2024  ± 1 day

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,222 Reviews)

    Page 2 of 12 • 270 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    37' Luxury Sailboat with Captain in Chicago, Illinois
    Sailing in United States · 10 guests

    37' Luxury Sailboat with Captain in Chicago, Illinois

    5.0
    Superowner
    $299hour
    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
    Events in United States · 12 guests

    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

    4.9
    Superowner
    Best of 2023
    $250hour
    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 Express 390 Luxury Charter in Chicago, Illinois
    Events in United States · 12 guests

    Sea Ray Express 390 Luxury Charter in Chicago, Illinois

    5.0
    $300hour
    UP to 20 passengers Party Boat - Chicago Playpen or River trips
    Powerboats in United States · 20 guests

    UP to 20 passengers Party Boat - Chicago Playpen or River trips

    5.0
    Superowner
    Best of 2023
    $120person
    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
    Maxum Yacht 44' in Chicago
    Events in United States · 13 guests

    Maxum Yacht 44' in Chicago

    5.0
    Superowner
    Best of 2023
    $268-$300hour
    Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties
    Events in United States · 12 guests

    Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

    5.0
    Best of 2023
    $400hour
    Instant Book
    Sea Ray 40ft - Luxurious, Spacious, Affordable
    Events in United States · 12 guests

    Sea Ray 40ft - Luxurious, Spacious, Affordable

    4.9
    $250hour
    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
    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
    42FT Regal Commodore Express Cruiser
    Events in United States · 12 guests

    42FT Regal Commodore Express Cruiser

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    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
    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
    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
    Chicago Playpen and River cruises! 35’
    Powerboats in United States · 10 guests

    Chicago Playpen and River cruises! 35’

    4.9
    $295hour
    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
    Luxurious 60' Yacht with Fly Bridge
    Events in United States · 12 guests

    Luxurious 60' Yacht with Fly Bridge

    5.0
    $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
    33ft Day Boat in Chicago
    Events in United States · 10 guests

    33ft Day Boat in Chicago

    4.9
    $275hour
    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
    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
    62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois
    Events in United States · 12 guests

    62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois

    New
    Superowner
    $800hour
    "Excelling in Excellence" Yacht Charter in Chicago, IL
    Events in United States · 13 guests

    "Excelling in Excellence" Yacht Charter in Chicago, IL

    New
    $772hour

    Chicago Reviews

    1. 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!

    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. MC

      Megan

      37' Luxury Sailboat with Captain in Chicago, Illinois

      Greg was an amazing captain - he sent a very helpful document that outlined all the details about the boat ahead of time, he was on time and willing to be flexible in wherever we wanted to go. We had an amazing time and I would definitely hire him again!

    4. Sara

      Sara

      37' Luxury Sailboat with Captain in Chicago, Illinois

      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😍

    5. GM

      Gerald

      37' Luxury Sailboat with Captain in Chicago, Illinois

      We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

    6. Bailey

      Bailey

      37' Luxury Sailboat with Captain in Chicago, Illinois

      We had such a good time taking our engagement photos on the boat. Greg was so accommodating to us with taking the photos and positioning the boat where we needed it. Would 100% recommend to anyone looking to take some amazing photos and have a great time on the lake.

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