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    $100-$300

    Rent a Boat or Yacht in Chicago, Illinois

    4.9(Average of 2,525 reviews in this area)•
    Boat Rentals,the United States,Illinois,Chicago
    Page 1 of 6 (140 listings)
    Captain Memo's 28 ft. Sea Ray in Chicago
    Events in Chicago · 6 guests

    Captain Memo's 28 ft. Sea Ray in Chicago

    5.0
    Superowner
    $230hour
    Maxum 2400 Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 8 guests

    Maxum 2400 Motor Yacht Rental in Chicago, Illinois

    3.5
    $150hour
    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
    $250hour
    32' Motor Yacht Charter Downtown Chicago's Lake Front, Relax And Enjoy The Day
    Events in Chicago · 6 guests

    32' Motor Yacht Charter Downtown Chicago's Lake Front, Relax And Enjoy The Day

    4.9
    Best of 2023
    $280hour
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
    Sailing in Chicago · 6 guests

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

    5.0
    Superowner
    Best of 2023
    $220hour
    Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois
    Tours in Chicago · 9 guests

    Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

    5.0
    $250hour
    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
    Powerboats in Chicago · 7 guests

    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

    5.0
    $150hour
    $200 Captain Included. 2021 Yamaha. Playpen, Fireworks, Skyline Cruises
    Powerboats in Chicago · 6 guests

    $200 Captain Included. 2021 Yamaha. Playpen, Fireworks, Skyline Cruises

    5.0
    $200hour
    Includes Fuel Sundancer 36' LOA
    Events in Chicago · 13 guests

    Includes Fuel Sundancer 36' LOA

    5.0
    $240-$250hour
    Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
    Events in Chicago · 13 guests

    Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

    4.9
    Superowner
    $275hour
    33' Formula Motor Yacht, Great for Playpen!
    Events in Chicago · 10 guests

    33' Formula Motor Yacht, Great for Playpen!

    5.0
    $150hour
    Private Cruise onboard Hunter Legend Sailboat in Chicago
    Sailing in Chicago · 6 guests

    Private Cruise onboard Hunter Legend Sailboat in Chicago

    5.0
    Superowner
    $200hour
    SEPTEMBER SPECIALS! Cruise or Party Chi-Town in Comfort & Style
    Powerboats in Chicago · 10 guests

    SEPTEMBER SPECIALS! Cruise or Party Chi-Town in Comfort & Style

    New
    $200hour
    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

    5.0
    Superowner
    Best of 2023
    $230hour
    **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
    Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago!
    Events in Chicago · 13 guests

    Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago!

    5.0
    Superowner
    $275hour
    *** $199 hr***Weekend Charter Rental - 33' Maxum!
    Events in Chicago · 10 guests

    *** $199 hr***Weekend Charter Rental - 33' Maxum!

    4.8
    $175hour
    Multi Level Luxury Yacht Rental in Chicago - Water toys are included!
    Events in Chicago · 12 guests

    Multi Level Luxury Yacht Rental in Chicago - Water toys are included!

    4.9
    Superowner
    Best of 2023
    $199hour
    42FT Regal Commodore Express Cruiser
    Events in Chicago · 12 guests

    42FT Regal Commodore Express Cruiser

    5.0
    Superowner
    Best of 2023
    $245-$275hour
    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
    $300hour
    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 2023
    $300-$399hour
    25ft Captained party and sightseeing boat!!!
    Powerboats in Chicago · 6 guests

    25ft Captained party and sightseeing boat!!!

    4.9
    Superowner
    $180hour
    Enjoy Chicago! 31' Beautiful Sea Ray Sun Dancer - Perfect for any Occasion
    Events in Chicago · 10 guests

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

    4.9
    Best of 2023
    $275-$300hour
    Instant Book
    Playpen bound on 25' Yamaha Jetboat!
    Powerboats in Chicago · 10 guests

    Playpen bound on 25' Yamaha Jetboat!

    5.0
    $225hour

    Chicago Reviews

    1. 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!

    2. 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!!

    3. BS
      Berin
      Captain Memo's 28 ft. Sea Ray in Chicago

      If you click out of Memo's page without booking, you're making a mistake! Memo was BEYOND anything my family could have imagined. Our group of 5 had one of the best times on his boat and he is the DEFINITION of hospitality. Memo is a GEM!!!!!!! BOOK WITH HIM!!!!!!

    4. GM
      Gwyn
      Captain Memo's 28 ft. Sea Ray in Chicago

      Couldn’t ask for a better cap to a first weekend experiencing Chicago. Captain Memo went out of his way to make the experience special, from making sure we always had a full drink in hand, to creating some Titanic-esque front of boat moments, to letting us take a turn at the helm. He even voluntarily let our time run long because we were all vibing to Frank Sinatra on the way back in to the docks. You will have a great time because he’s just a generally kind soul. Oh captain my captain!

    5. LB
      Laura
      Captain Memo's 28 ft. Sea Ray in Chicago

      We had an absolute blast with Captain Memo! He is the most accommodating and kind person and went above and beyond many times over to make our experience one of the best times we could ever imagine. We can’t recommend him highly enough! Thank you Captain Memo!

    6. HG
      Harsha
      Captain Memo's 28 ft. Sea Ray in Chicago

      This was our first time on a boat all for ourselves. I planned to celebrate my fiancé s birthday on the boat. I wanted to cut the cake on the boat at the Playpen . Captain Memo was so accommodating and very easy to work with. He made the trip a memorable and fun experience. Overall definitely recommended. We will return back soon

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