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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,712 Reviews)

    Page 10 of 12 • 280 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL
    Events in Chicago · 13 guests

    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL

    New
    $1,089/hour
    Catamaran Sailing Lessons Chicago
    Tours in Chicago · 6 guests

    Catamaran Sailing Lessons Chicago

    New
    $350+/hour
    Limited Availability
    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat
    Powerboats in Chicago · 12 guests

    Luxury on the Lakefront | Playpen | Chicago River | 25' Monterey Captained Boat

    New
    $250/hour
    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan
    Events in Chicago · 12 guests

    Premium 55' Sea Ray Yacht Charter - Seakeeper Stability, Chicago Lake Michigan

    New
    $1,404/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
    Limited Availability
    46ft Luxury Sea Ray 410 Express Cruiser Yacht Chicago for 13 Guests
    Events in Chicago · 13 guests

    46ft Luxury Sea Ray 410 Express Cruiser Yacht Chicago for 13 Guests

    New
    $250/hour
    Instant Book
    Limited Availability
    Explore the Famous Chicago Playpen! 34' Rinker Fiesta Vee Motor Yacht- 12 Guests
    Events in Chicago · 12 guests

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

    New
    Superowner
    Best of 2026
    $160+/hour
    Instant Book
    Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests
    Events in Chicago · 10 guests

    Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests

    New
    $200/hour
    High Demand
    Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht
    Events in Chicago · 13 guests

    Chicago's Newest 40ft Sea Ray Sundancer Luxury Motor Yacht

    New
    $250/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
    40 feet of Lights, Music, and Fun!!!
    Powerboats in Chicago · 12 guests

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

    New
    Superowner
    $250/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
    Beautiful Sea Ray 390 Express Cruiser Yacht for 12 Guests in Chicago
    Events in Chicago · 12 guests

    Beautiful Sea Ray 390 Express Cruiser Yacht for 12 Guests in Chicago

    New
    $250/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 37' Sea Ray Sundancer Perfect for Any Occasion In Chicago
    Events in Chicago · 12 guests

    Beautiful 37' Sea Ray Sundancer Perfect for Any Occasion In Chicago

    New
    $300/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
    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
    Limited Availability
    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
    26’ Sea Ray 240 Sundeck
    Powerboats in Chicago · 10 guests

    26’ Sea Ray 240 Sundeck

    1.0
    $225/hour
    36’ Yacht for 12 Guests | Playpen Party, BYOB & Captain Included In Chicago
    Events in Chicago · 12 guests

    36’ Yacht for 12 Guests | Playpen Party, BYOB & Captain Included In Chicago

    New
    $500/hour
    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor
    Events in Chicago · 13 guests

    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor

    New
    $250/hour
    Instant Book
    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
    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
    Events in Chicago · 13 guests

    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

    New
    $1,190/hour

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