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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (5,032 Reviews)

    Page 2 of 11 • 250 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Li'l Red, Crownline CR250 Cabin Cruiser.
    Powerboats in Chicago · 10 guests

    Li'l Red, Crownline CR250 Cabin Cruiser.

    5.0
    Best of 2025
    $325/hour
    Instant Book
    Maxum Yacht 44' in Chicago
    Powerboats in Chicago · 13 guests

    Maxum Yacht 44' in Chicago

    4.9
    Superowner
    Best of 2025
    $268/hour
    SeaRay Sundancer 340 Motor Yacht
    Events in Chicago · 12 guests

    SeaRay Sundancer 340 Motor Yacht

    3.6
    $250/hour
    Playpen bound on 25' Yamaha Jetboat!
    Powerboats in Chicago · 10 guests

    Playpen bound on 25' Yamaha Jetboat!

    5.0
    $245/hour
    27' Chris Craft with Water Toys plus Jet Ski Available
    Powerboats in Chicago · 6 guests

    27' Chris Craft with Water Toys plus Jet Ski Available

    4.9
    Superowner
    $240/hour
    Instant Book
    25ft Rinker - Captained included in price- Chicago
    Powerboats in Chicago · 8 guests

    25ft Rinker - Captained included in price- Chicago

    4.9
    Superowner
    $199/hour
    Instant Book
    46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 13 guests

    46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

    5.0
    Superowner
    $300/hour
    Instant Book
    Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
    Events in Chicago · 8 guests

    Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

    5.0
    $225/hour
    Summertime Chi Vibes - Soak up the Sun in Style!
    Powerboats in Chicago · 6 guests

    Summertime Chi Vibes - Soak up the Sun in Style!

    5.0
    $300/hour
    50' Multi-level Luxury Yacht with Party up to 12
    Events in Chicago · 12 guests

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

    5.0
    Superowner
    Best of 2025
    $350/hour
    Instant Book
    38-ft Party Pontoon for Up to 20 Guests in Chicago
    Powerboats in Chicago · 20 guests

    38-ft Party Pontoon for Up to 20 Guests in Chicago

    5.0
    Superowner
    Best of 2025
    $680/hour
    **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
    $295+/hour
    39' Sea Ray for Rent in Chicago, Illinois!
    Events in Chicago · 12 guests

    39' Sea Ray for Rent in Chicago, Illinois!

    5.0
    $350+/hour
    Instant Book
    2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
    Events in Chicago · 11 guests

    2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

    5.0
    $250/hour
    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

    4.9
    Superowner
    Best of 2025
    $300/hour
    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!
    Events in Chicago · 13 guests

    'Aquaholic' 40' Sea Ray Captained Charter on with all amenities in Chicago!

    5.0
    Superowner
    $350/hour
    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

    4.6
    $250/hour
    Instant Book
    Burnham Harbor, CAPTAIN/FUEL INCLUDED
    Events in Chicago · 7 guests

    Burnham Harbor, CAPTAIN/FUEL INCLUDED

    5.0
    $250+/hour
    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
    Powerboats in Chicago · 12 guests

    Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

    5.0
    Superowner
    Best of 2025
    $210/hour
    Double Decker 50ft Sea Ray Flybridge Yacht!
    Events in Chicago · 13 guests

    Double Decker 50ft Sea Ray Flybridge Yacht!

    5.0
    Superowner
    Best of 2025
    $292/hour
    36ft Carver Mariner Motor Yacht in Chicago
    Events in Chicago · 12 guests

    36ft Carver Mariner Motor Yacht in Chicago

    4.8
    $350/hour
    Instant Book
    7 to 13 passenger Lake Michigan Sailing Charter
    Sailing in Chicago · 13 guests

    7 to 13 passenger Lake Michigan Sailing Charter

    5.0
    $550/hour
    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

    4.9
    $250/hour
    Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior
    Events in Chicago · 13 guests

    Gorgeous Sea Ray Sundancer 40ft in Chicago with Stunning Interior

    5.0
    Superowner
    Best of 2025
    $245/hour

    Chicago Reviews

    1. JS

      Jessica

      46' Spacious Portofino Party Yacht in Chicago For Every Occasion

      We had such a great time! Kyle was great to work with and very responsive making the whole process easy. Captain G was awesome as well and really helped make the experience fun and smooth. We’ll definitely be booking the boat again! Highly recommend!

    2. KS

      Kathleen

      Li'l Red, Crownline CR250 Cabin Cruiser.

      Ariel was responsive and ensured we still got out and had a great day on the water, despite emergency circumstances that easily could have ruined the day. I very much recommend the experience.

    3. SL

      Samantha

      27' Chris Craft with Water Toys plus Jet Ski Available

      We had a great day out on the water with Tim Jr! He was flexible with the weather, and had great suggestions for our group.

    4. DT

      Dana

      Double Decker 50ft Sea Ray Flybridge Yacht!

      Had a great time on Chris’s boat. The instructions were clear, communication was direct and we had a wonderful time!

    5. Courtney

      Courtney

      Maxum Yacht 44' in Chicago

      We had the very best time on this boat! Chris and the captain, Sean, were awesome. We can’t wait to go back!

    6. Jene

      Jene

      27' Chris Craft with Water Toys plus Jet Ski Available

      He was amazing and accommodating, took great pics and was really funny. Highly recommend.

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