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    $100-$300

    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (2,711 Reviews)

    Page 3 of 7 • 146 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

    5.0
    Superowner
    Best of 2023
    $250hour
    Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
    Powerboats in Chicago · 12 guests

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

    4.8
    Superowner
    $250hour
    Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois
    Sailing in Chicago · 6 guests

    Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

    5.0
    $225hour
    40ft Boat w/ HUGE open seating area!
    Events in Chicago · 12 guests

    40ft Boat w/ HUGE open seating area!

    5.0
    Superowner
    Best of 2023
    $210-$240hour
    53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    53' Luxury Yacht w/Flybridge and Sundeck Rental in Chicago, Illinois

    5.0
    Superowner
    $300-$400hour
    44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!
    Events in Chicago · 12 guests

    44ft of Luxury Yachting! Ask About Pre-Boating Season Discounts!!

    5.0
    $250hour
    50' Sea Ray-12 Passengers *BELIEVE CHICAGO*
    Events in Chicago · 12 guests

    50' Sea Ray-12 Passengers *BELIEVE CHICAGO*

    4.9
    Superowner
    Best of 2023
    $300hour
    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser
    Events in Chicago · 12 guests

    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser

    5.0
    Superowner
    $250hour
    Set Sail with 36' Sailing Boat in Downtown, Chicago
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago

    5.0
    Superowner
    $225hour
    Luxury 33' Sea Ray - Come Charter & See Chicago!
    Events in Chicago · 8 guests

    Luxury 33' Sea Ray - Come Charter & See Chicago!

    5.0
    $267hour
    Charter a 31' Pearson Cruising Sloop, Chicago
    Sailing in Chicago · 6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    4.5
    Superowner
    $200hour
    55' Carver Yacht-12 Passengers* Chicago Vibes
    Events in Chicago · 12 guests

    55' Carver Yacht-12 Passengers* Chicago Vibes

    4.8
    Superowner
    Best of 2023
    $300hour
    31' Captained Sea Ray Sundancer, Fun in Chicago Aboard
    Powerboats in Chicago · 6 guests

    31' Captained Sea Ray Sundancer, Fun in Chicago Aboard

    4.8
    $250hour
    Fuel & Lily Pad Included on 37' Four Winns 348 Vista Yacht!
    Events in Chicago · 12 guests

    Fuel & Lily Pad Included on 37' Four Winns 348 Vista Yacht!

    4.3
    $300hour
    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois
    Powerboats in Chicago · 8 guests

    Captained 27ft Bayliner Ciera Yacht in Chicago, Illinois

    5.0
    $250hour
    61’ Gorgeous Sunseeker Predator Fantastic Condition Weekday Special Rates!
    Events in Chicago · 12 guests

    61’ Gorgeous Sunseeker Predator Fantastic Condition Weekday Special Rates!

    4.7
    $250hour
    37' Spacious Party Yacht For Every Occasion
    Events in Chicago · 12 guests

    37' Spacious Party Yacht For Every Occasion

    5.0
    $225hour
    26' Formula Yacht Is Ready For Fun in Chicago
    Events in Chicago · 12 guests

    26' Formula Yacht Is Ready For Fun in Chicago

    4.9
    $250hour
    Summertime Chi Ready!!
    Events in Chicago · 12 guests

    Summertime Chi Ready!!

    5.0
    $200hour
    Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    Luxury 40 ft. Sea Ray Sundancer Motor Yacht in Chicago, Illinois

    5.0
    $300hour
    Doral Alegria 50' Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    Doral Alegria 50' Yacht in Chicago, Illinois

    5.0
    $275hour
    32ft SeaRay Sundancer for Charter in Chicago
    Events in Chicago · 6 guests

    32ft SeaRay Sundancer for Charter in Chicago

    5.0
    $300hour
    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
    Events in Chicago · 12 guests

    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    5.0
    Superowner
    Best of 2023
    $250hour
    34' of Lakefront Fun! Music Lights and a Great time!!!
    Powerboats in Chicago · 12 guests

    34' of Lakefront Fun! Music Lights and a Great time!!!

    New
    Superowner
    $300hour

    Chicago Reviews

    1. SG

      Samuel

      50' Sea Ray-12 Passengers *BELIEVE CHICAGO*

      Captain Carlos was great at communicating with us leading up to the event and he made the experience better than expected. I would highly recommend him.

    2. SH

      Susan

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      A wonderful May sail. Great boat for 6 people to relax and enjoy the city skyline, while Ray tends to the sailing. Very competent sailor and friendly.

    3. HW

      Hector

      Set Sail with 36' Sailing Boat in Downtown, Chicago

      Very professional and yet easygoing captain. Boat was very nice - in excellent shape and well maintained. Highly recommend! We will be back again.

    4. CP

      Carly

      38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

      We had such a great time with Captain Steve! He made everything so easy by communicating exactly where we should get dropped off, how to get our food and drinks to the boat easily and took us on an awesome city river tour. They made up for the fact that we weren’t able to anchor due to the wind and rough waves. 10/10 would book again!

    5. CC

      Christine

      38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

      Rented a night charter for July 4 with Captain Steve. Had an amazing time with friends! Captain Steve was a pleasure to work with and attended to all of our needs. The float pad and water toys were fun to have. Though Navy Pier no longer displayed fireworks for Independence Day, Captain Steve made sure we were able to view multiple shows from a distance. We will definitely book this charter again for future events!

    6. Mary Kaylle

      Mary Kaylle

      38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

      It was an amazing experience! The yacht was perfect— the lily pad, space, accommodations, etc. And captain Steve was so fun and kind. My guests and I had such a great time. We plan to do it all again!! Definitely worth the 1 hr extension for the golden hour/sunset!!

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