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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (5,722 Reviews)

    Page 10 of 12 • 272 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Experience Lake Michigan like never before!!!!!
    Events in Chicago · 8 guests

    Experience Lake Michigan like never before!!!!!

    New
    $225/hour
    55' Sea Ray Motor Yacht Bareboat Charter in Chicago
    Events in Chicago · 12 guests

    55' Sea Ray Motor Yacht Bareboat Charter in Chicago

    New
    $1,337/hour
    Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois
    Events in Chicago · 12 guests

    Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois

    New
    $500+/hour
    34' Luxury Sea Ray Sundancer Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    34' Luxury Sea Ray Sundancer Yacht Rental in Chicago, Illinois

    New
    $339+/hour
    26’ Sea Ray 240 Sundeck
    Powerboats in Chicago · 10 guests

    26’ Sea Ray 240 Sundeck

    1.0
    $225/hour
    Catamaran Sailing Lessons Chicago
    Tours in Chicago · 6 guests

    Catamaran Sailing Lessons Chicago

    New
    Best of 2025
    $350+/hour
    Beautiful 40ft Sea Ray Yacht
    Events in Chicago · 12 guests

    Beautiful 40ft Sea Ray Yacht

    New
    $250/hour
    36ft Luxury Silverton Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    36ft Luxury Silverton Motor Yacht Rental in Chicago, Illinois

    New
    $275/hour
    44 foot Cabin Cruiser for rent in Chicago $250/hr
    Events in Chicago · 12 guests

    44 foot Cabin Cruiser for rent in Chicago $250/hr

    5.0
    $350/hour
    41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
    Powerboats in Chicago · 12 guests

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

    5.0
    Superowner
    $390+/hour
    Come enjoy fun in the sun on our 30 ft Bayliner Ciera 8-10 ppl
    Events in Chicago · 10 guests

    Come enjoy fun in the sun on our 30 ft Bayliner Ciera 8-10 ppl

    New
    $200/hour
    Instant Book
    40 feet of Lights, Music, and Fun!!!
    Powerboats in Chicago · 12 guests

    40 feet of Lights, Music, and Fun!!!

    New
    Superowner
    Best of 2025
    $350/hour
    46' luxury yacht for up to 12 people - DUSABLE Harbor
    Events in Chicago · 12 guests

    46' luxury yacht for up to 12 people - DUSABLE Harbor

    New
    $280/hour
    62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois
    Events in Chicago · 13 guests

    62' Azimut Flybridge Italian Luxury Yacht for Rent (MPY#6) in Chicago, Illinois

    New
    $800/hour
    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee - 12 Guests
    Powerboats in Chicago · 12 guests

    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee - 12 Guests

    New
    Superowner
    Best of 2025
    $275+/hour
    Enjoy "The Good Life" - 35' Four Winns
    Powerboats in Chicago · 8 guests

    Enjoy "The Good Life" - 35' Four Winns

    New
    $458/hour
    See Chicago like no one else can
    Events in Chicago · 12 guests

    See Chicago like no one else can

    New
    $300+/hour
    Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay
    Events in Chicago · 12 guests

    Make no mistake. She is clean with plenty of room and monster sounds. 40’ searay

    New
    $400/hour
    Beautiful Sea Ray 320 Sundancer Inboard Boat
    Events in Chicago · 10 guests

    Beautiful Sea Ray 320 Sundancer Inboard Boat

    New
    $225/hour
    New listing 40' Regal luxury Yacht
    Events in Chicago · 12 guests

    New listing 40' Regal luxury Yacht

    New
    $400/hour
    44ft Premium Luxury Chris Craft Yacht
    Events in Chicago · 12 guests

    44ft Premium Luxury Chris Craft Yacht

    New
    $278/hour
    Beautiful 37' Sea Ray Sundancer Perfect for ANY Occasion!
    Events in Chicago · 12 guests

    Beautiful 37' Sea Ray Sundancer Perfect for ANY Occasion!

    New
    $300/hour
    Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun
    Powerboats in Hammond · 10 guests

    Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun

    New
    $350/hour
    42' Luxurious Meridian Flybridge Yacht
    Events in Chicago · 12 guests

    42' Luxurious Meridian Flybridge Yacht

    5.0
    $500/hour

    Chicago Reviews

    1. RC

      Rob

      42' Luxurious Meridian Flybridge Yacht

      Great time - fantastic captain and very professional. A pleasure to work with - I highly recommend

    2. MW

      Maggie

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

      Very easy process. Nice people to work with.

    3. KG

      Karan

      44 foot Cabin Cruiser for rent in Chicago $250/hr

      Great overall experience

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