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    Rent a Boat or Yacht in Chicago, Illinois

    4.9
    (1,327 Reviews)

    Page 3 of 3 • 64 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    Instant Book
    37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen
    Events in Chicago · 12 guests

    37' Beautiful Sea Ray Venture - Explore Chicago's Famous Playpen

    New
    Superowner
    Best of 2025
    $400/hour
    Instant Book
    No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

    New
    $245/hour
    Instant Book
    Private 44' Yacht - Free Champagne, Free Fuel, Free Floating Island
    Events in Chicago · 12 guests

    Private 44' Yacht - Free Champagne, Free Fuel, Free Floating Island

    New
    $375/hour
    Instant Book
    Enjoy Chicago in this 46' Sea Ray - Great for Birthdays - Bachelorette Parties
    Events in Chicago · 12 guests

    Enjoy Chicago in this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

    New
    Superowner
    Best of 2025
    $400/hour
    Instant Book
    40' Carver Yacht with space all around
    Events in Chicago · 12 guests

    40' Carver Yacht with space all around

    New
    $375/hour
    Instant Book
    Luxury Unleashed – 40ft Sea Ray Dream Cruiser
    Events in Chicago · 12 guests

    Luxury Unleashed – 40ft Sea Ray Dream Cruiser

    New
    $450/hour
    Instant Book
    49 Passenger 57' Power Catamaran - Perfect For Events!
    Events in Chicago · 49 guests

    49 Passenger 57' Power Catamaran - Perfect For Events!

    New
    Superowner
    $1,750/hour
    Instant Book
    Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!
    Events in Chicago · 12 guests

    Enjoy Chicago in this 42' Stunning Sea Ray Sun Dancer - Great for any Event!

    New
    Superowner
    Best of 2025
    $400/hour
    Instant Book
    Big Party Boat for up to 24 people - at Navy Pier Marina
    Events in Chicago · 24 guests

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

    New
    $1,136/hour
    Instant Book
    49 Passenger 72' Chris Craft - Perfect for Events!
    Events in Chicago · 49 guests

    49 Passenger 72' Chris Craft - Perfect for Events!

    New
    Superowner
    $2,000/hour
    Instant Book
    31ft Cabin Cruiser Belmont Harbor location
    Events in Chicago · 6 guests

    31ft Cabin Cruiser Belmont Harbor location

    New
    $300/hour
    Instant Book
    Chicago Water Music on the Chicago River Scenic River cruises with live music
    Powerboats in Chicago · 19 guests

    Chicago Water Music on the Chicago River Scenic River cruises with live music

    New
    $800+/hour
    Instant Book
    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois

    5.0
    Snoozed - Active 03 Aug 2025
    42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR
    Events in Chicago · 12 guests

    42' Sea Ray Sundancer Luxury Yacht - Great for outings! DIVERSEY HARBOR

    New
    Snoozed - Active 02 Aug 2025
    Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures
    Events in Chicago · 12 guests

    Spacious 37' Rinker Express - Perfect for Lake Michigan Adventures

    New
    Snoozed - Active 02 Nov 2025

    Chicago Reviews

    1. KJ

      Kyle

      Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois

      The owner was very responsive and communication was on point. The price of this vessel compared to others is a great deal. Captain Joe was a cool dude and made sure we were taken care of. I recommend booking.

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