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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,628 Reviews)

    Page 10 of 12 • 273 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee - 12 Guests
    Events in Chicago · 12 guests

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

    New
    Superowner
    Best of 2026
    $280+/hour
    Instant Book
    Chicago Luxury Yacht Charter Chris-Craft | 12 Guests | Playpen and River Cruises
    Events in Chicago · 12 guests

    Chicago Luxury Yacht Charter Chris-Craft | 12 Guests | Playpen and River Cruises

    New
    $250/hour
    New 40ft Regal Luxury Yacht For 12 People in Chicago
    Events in Chicago · 12 guests

    New 40ft Regal Luxury Yacht For 12 People in Chicago

    New
    $260+/hour
    Limited Availability
    44ft Premium Luxury Chris Craft Yacht
    Events in Chicago · 12 guests

    44ft Premium Luxury Chris Craft Yacht

    New
    $278/hour
    40 feet of Lights, Music, and Fun!!!
    Powerboats in Chicago · 12 guests

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

    New
    Superowner
    $250/hour
    Beautiful 40ft Sea Ray Yacht
    Events in Chicago · 12 guests

    Beautiful 40ft Sea Ray Yacht

    New
    $220/hour
    Limited Availability
    Charter on Lake Michigan and the Chicago River | Sea Ray 300 Sundancer
    Powerboats in Chicago · 12 guests

    Charter on Lake Michigan and the Chicago River | Sea Ray 300 Sundancer

    New
    $260+/hour
    Chicago Skyline Sea Ray Yacht Experience on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago Skyline Sea Ray Yacht Experience on Lake Michigan!

    New
    $275/hour
    Limited Availability
    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 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
    Tour Chicago On Our Beautiful 31ft Sea Ray Sundancer
    Events in Chicago · 10 guests

    Tour Chicago On Our Beautiful 31ft Sea Ray Sundancer

    New
    $200/hour
    Chicago's 43' Tiara Luxury Getaway on Lake Michigan for Groups & Family
    Events in Chicago · 12 guests

    Chicago's 43' Tiara Luxury Getaway on Lake Michigan for Groups & Family

    New
    $605/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
    $350/hour
    Come Cruise the waters around Chicago with 33ft Motor Yacht
    Powerboats in Chicago · 6 guests

    Come Cruise the waters around Chicago with 33ft Motor Yacht

    New
    $325/hour
    26’ Sea Ray 240 Sundeck
    Powerboats in Chicago · 10 guests

    26’ Sea Ray 240 Sundeck

    1.0
    $225/hour
    Captained Charter | 62' Azimut Luxury Yacht Rental
    Events in Chicago · 13 guests

    Captained Charter | 62' Azimut Luxury Yacht Rental

    New
    $1,190/hour
    Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport
    Events in Chicago · 12 guests

    Scenic Lake Michigan Cruises on a 35’ Formula Sun Sport

    New
    $350/hour
    Chicago Yacht Experience – Private Charter | 54’ Neptunus Express
    Events in Chicago · 12 guests

    Chicago Yacht Experience – Private Charter | 54’ Neptunus Express

    New
    $300/hour
    INCLUDES TIP - No tie ups - 40ft Yacht - lots of room for 13 - DuSable Harbor
    Events in Chicago · 13 guests

    INCLUDES TIP - No tie ups - 40ft Yacht - lots of room for 13 - DuSable Harbor

    New
    $250/hour
    Instant Book
    Sail away in Luxury | 30’ Bayliner Yacht | 12 Passenger
    Events in Chicago · 12 guests

    Sail away in Luxury | 30’ Bayliner Yacht | 12 Passenger

    New
    $350/hour
    SeaDoo GTI SE 170 Jet ski rental in Chicago
    Water Sports in Chicago · 2 guests

    SeaDoo GTI SE 170 Jet ski rental in Chicago

    New
    $180/hour
    INCLUDES TIP - Big Party Boat for up to 24 people - at Navy Pier Marina
    Events in Chicago · 24 guests

    INCLUDES TIP - Big Party Boat for up to 24 people - at Navy Pier Marina

    New
    $1,136/hour
    Instant Book
    2023 Sea Doo Gti90 Jetski In Indiana or Chicago
    Water Sports in Hammond · 3 guests

    2023 Sea Doo Gti90 Jetski In Indiana or Chicago

    New
    $160/hour
    100 Passenger 75' Power Catamaran - Perfect for Events!
    Events in Chicago · 100 guests

    100 Passenger 75' Power Catamaran - Perfect for Events!

    New
    Superowner
    $1,600/hour

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