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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (5,763 Reviews)

    Page 10 of 12 • 275 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Explore the Chicago Playpen! 46ft Sea Ray - Lily Pad Included!
    Powerboats in Chicago · 12 guests

    Explore the Chicago Playpen! 46ft Sea Ray - Lily Pad Included!

    5.0
    Superowner
    Best of 2025
    $390/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
    Catamaran Sailing Lessons Chicago
    Tours in Chicago · 6 guests

    Catamaran Sailing Lessons Chicago

    New
    Best of 2025
    $350+/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
    26’ Sea Ray 240 Sundeck
    Powerboats in Chicago · 10 guests

    26’ Sea Ray 240 Sundeck

    1.0
    $225/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
    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
    Chicago’s Casual Lakefront Escape
    Events in Chicago · 12 guests

    Chicago’s Casual Lakefront Escape

    New
    $425/hour
    Beautiful 40ft Sea Ray Yacht
    Events in Chicago · 12 guests

    Beautiful 40ft Sea Ray Yacht

    New
    $250/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
    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
    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
    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

    5.0
    $458/hour
    See Chicago like no one else can
    Events in Chicago · 12 guests

    See Chicago like no one else can

    New
    $300+/hour
    New listing 40' Regal luxury Yacht
    Events in Chicago · 12 guests

    New listing 40' Regal luxury Yacht

    New
    $350/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

    5.0
    $400/hour
    Beautiful Sea Ray 320 Sundancer Inboard Boat
    Events in Chicago · 10 guests

    Beautiful Sea Ray 320 Sundancer Inboard Boat

    New
    $225/hour
    44ft Premium Luxury Chris Craft Yacht
    Events in Chicago · 12 guests

    44ft Premium Luxury Chris Craft Yacht

    New
    $278/hour
    Capt. Included - 10 Passengers - 27' Bayliner Ciera Charter Boat
    Powerboats in Chicago · 10 guests

    Capt. Included - 10 Passengers - 27' Bayliner Ciera Charter Boat

    New
    $248/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
    Polynesian Party Boat, up to 6 people, captain and drink package included!
    Powerboats in Chicago · 6 guests

    Polynesian Party Boat, up to 6 people, captain and drink package included!

    New
    $250/hour
    Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago Illinois
    Events in Chicago · 12 guests

    Beautiful 39ft Double Decker Carver Mariner Luxury Yacht in Chicago Illinois

    New
    $325/hour

    Chicago Reviews

    1. JG

      Jennifer

      Enjoy "The Good Life" - 35' Four Winns

      boat good size for our group of 10, was disappointed we could not sit on the back of the boat while sailing...it would have helped with the space for our group and the experience, especially at night. Roger our captain was wonderful - polite, professional, made our safety first

    2. KG

      Karan

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

      Great overall experience

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