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    $100-$300

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (2,445 Reviews)

    Page 1 of 6 • 139 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Captain Memo's 28 ft. Sea Ray in Chicago
    Events in Chicago · 8 guests

    Captain Memo's 28 ft. Sea Ray in Chicago

    5.0
    Superowner
    $250hour
    Instant Book
    27' Maxum 2400 Motor Yacht Rental in Chicago
    Events in Chicago · 8 guests

    27' Maxum 2400 Motor Yacht Rental in Chicago

    3.5
    $200hour
    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
    32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
    Events in Chicago · 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 Chicago · 8 guests

    Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

    5.0
    $225hour
    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
    Powerboats in Chicago · 6 guests

    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

    5.0
    $175hour
    *** $175 to $199 hr***Weekend Charter Rental - 33' Maxum!
    Events in Chicago · 10 guests

    *** $175 to $199 hr***Weekend Charter Rental - 33' Maxum!

    4.8
    $175hour
    Playpen bound on 25' Yamaha Jetboat!
    Powerboats in Chicago · 10 guests

    Playpen bound on 25' Yamaha Jetboat!

    5.0
    $225hour
    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
    Double Decker 50FT Sea Ray Flybridge Yacht!
    Events in Chicago · 13 guests

    Double Decker 50FT Sea Ray Flybridge Yacht!

    5.0
    Superowner
    Best of 2023
    $292hour
    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
    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
    Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)
    Events in Chicago · 12 guests

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

    4.9
    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
    36' Sundancer in Chicago
    Events in Chicago · 13 guests

    36' Sundancer in Chicago

    5.0
    $240-$250hour
    UP to 20 passengers Party Boat - Chicago Playpen or River trips
    Powerboats in Chicago · 20 guests

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

    5.0
    Superowner
    Best of 2023
    $120person
    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
    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
    Superowner
    $300hour
    Sea Ray 40ft - Luxurious, Spacious, Affordable
    Events in Chicago · 12 guests

    Sea Ray 40ft - Luxurious, Spacious, Affordable

    4.9
    $250hour
    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED
    Events in Chicago · 7 guests

    Beautiful Burnham Harbor, CAPTAIN & FUEL INCLUDED

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

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

    4.9
    Best of 2023
    $275-$300hour
    Instant Book
    37' Luxury Sailboat with Captain in Chicago, Illinois
    Sailing in Chicago · 10 guests

    37' Luxury Sailboat with Captain in Chicago, Illinois

    5.0
    Superowner
    $299hour
    33' Formula Motor Yacht - Great for Playpen!
    Events in Chicago · 10 guests

    33' Formula Motor Yacht - Great for Playpen!

    5.0
    $150hour

    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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