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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (4,222 Reviews)
    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated

    Most Popular Yachts in Chicago

    View All
    • 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
    • 55' Sea Ray Luxury Yacht in Chicago
      Events in United States · 12 guests

      55' Sea Ray Luxury Yacht in Chicago

      5.0
      $325hour
    • 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
    • Diversey Harbor 46 ft Luxury Yacht Sun Dancer
      Events in United States · 12 guests

      Diversey Harbor 46 ft Luxury Yacht Sun Dancer

      5.0
      $200hour
    • 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
    • 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
    • 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

    All Chicago Listings

    Page 1 of 12 • 270 listings

    Captain Memo's 28 ft. Sea Ray in Chicago
    Events in United States · 8 guests

    Captain Memo's 28 ft. Sea Ray in Chicago

    5.0
    Superowner
    $280hour
    Instant Book
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
    Sailing in United States · 6 guests

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    5.0
    Superowner
    Best of 2023
    $220hour
    24 Passenger Captained Party & Event Boat in Chicago!
    Powerboats in United States · 24 guests

    24 Passenger Captained Party & Event Boat in Chicago!

    5.0
    Superowner
    Best of 2023
    $800hour
    20 Passenger Captained Party & Event Boat in Chicago
    Powerboats in United States · 20 guests

    20 Passenger Captained Party & Event Boat in Chicago

    5.0
    Superowner
    Best of 2023
    $700hour
    2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
    Events in United States · 11 guests

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

    5.0
    Superowner
    Best of 2023
    $319hour
    Instant Book
    32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
    Events in United States · 6 guests

    32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

    4.9
    Best of 2023
    $280hour
    Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois
    Powerboats in United States · 8 guests

    Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

    5.0
    $225hour
    40ft Formula 40 Performance Cruiser in Chicago
    Tours in United States · 13 guests

    40ft Formula 40 Performance Cruiser in Chicago

    5.0
    Superowner
    Best of 2023
    $349hour
    61ft Premier Sea Ray Chicago Playpen, River, Winery
    Events in United States · 12 guests

    61ft Premier Sea Ray Chicago Playpen, River, Winery

    5.0
    Superowner
    Best of 2023
    $600hour
    Instant Book
    40' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Events in United States · 12 guests

    40' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

    5.0
    Superowner
    Best of 2023
    $400hour
    LUXURY - Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
    Powerboats in United States · 12 guests

    LUXURY - Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

    5.0
    Superowner
    $400hour
    38' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Events in United States · 12 guests

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

    New
    Superowner
    Best of 2023
    $400hour
    44' Sea Ray Express Luxury Motor Yacht Rental in Chicago
    Events in United States · 12 guests

    44' Sea Ray Express Luxury Motor Yacht Rental in Chicago

    4.8
    Superowner
    $399hour
    20 passengers Party Boat in Chicago
    Powerboats in United States · 20 guests

    20 passengers Party Boat in Chicago

    5.0
    Superowner
    Best of 2023
    $680hour
    Private Cruise onboard Hunter Legend Sailboat in Chicago
    Sailing in United States · 6 guests

    Private Cruise onboard Hunter Legend Sailboat in Chicago

    5.0
    Superowner
    $200hour
    35' Sea Ray SLX Motor Yacht Charter in Chicago
    Events in United States · 13 guests

    35' Sea Ray SLX Motor Yacht Charter in Chicago

    5.0
    Superowner
    Best of 2023
    $369hour
    Instant Book
    27' Chris Craft with Water Toys plus Jet Ski Available
    Powerboats in United States · 6 guests

    27' Chris Craft with Water Toys plus Jet Ski Available

    5.0
    Superowner
    Best of 2023
    $230hour
    14 Passenger Captained Party & Event Boat in Chicago, Illinois!
    Powerboats in United States · 14 guests

    14 Passenger Captained Party & Event Boat in Chicago, Illinois!

    5.0
    Superowner
    Best of 2023
    $600hour
    36' Sundancer in Chicago
    Events in United States · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$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
    70' EXCLUSIVE Motor Yacht NEW to Chicago
    Events in United States · 13 guests

    70' EXCLUSIVE Motor Yacht NEW to Chicago

    4.8
    Superowner
    $999hour
    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
    Powerboats in United States · 6 guests

    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

    5.0
    $170hour
    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
    33' Formula Motor Yacht - Great for Playpen!
    Events in United States · 10 guests

    33' Formula Motor Yacht - Great for Playpen!

    5.0
    $150hour
    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
    Events in United States · 7 guests

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

    5.0
    $300hour
    Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion
    Events in United States · 10 guests

    Enjoy Chicago! Beautiful 31' Sea Ray Sundancer - Perfect for any Occasion

    4.9
    Best of 2023
    $275-$300hour
    Instant Book
    **Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**
    Events in United States · 12 guests

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

    5.0
    Superowner
    Best of 2023
    $250hour
    25ft Rinker - Captained Party - Chicago
    Powerboats in United States · 6 guests

    25ft Rinker - Captained Party - Chicago

    4.9
    Superowner
    $180hour

    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. 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 :)

    3. SA

      Suchi

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

      Great trip and excellent service! Had such a fun time with my girlfriends on the water!

    4. EG

      Emily

      25ft Rinker - Captained Party - Chicago

      Had the best time! Joe was super helpful and super fun!

    5. Okoye'

      Okoye'

      Captain Memo's 28 ft. Sea Ray in Chicago

      Memo is absolutely amazing! Please believe every great review left. He gives outstanding instructions as to where and how to find his boat. He had a cooler, floats, a large speaker- essentially everything we needed. My friends and I had a great time and will be back!

    6. Molly

      Molly

      Captain Memo's 28 ft. Sea Ray in Chicago

      Captain Memo made this experience unforgettable, just like the name of his boat! He made sure we knew exactly where to meet him at the time of departure, supplied coolers and ice for us and had all the lake floats blown up and ready for us to relax in the lake. He is trustworthy and all around a great guy. Thank you Captain Memo for an unforgettable time!!

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