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Showing 157 - 168 of 467 results
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Showing 157 - 168 of 467 results
  • FXDC 2011 Super Glide® Custom $12,999.00 $8,499.00

    305933
    Pre-owned
    2011
    36542 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1GV417BC305933
    DK/LT ROOT BEER

    For riders who want a head start on building their dream custom motorcycle or for those who just want a little more straight from the showroom floor, the Dyna® Super Glide® Custom model may be the perfect bike. This stylish performer’s long, low profile is enhanced by a low-slung, two-up ribbed …

  • FXDBP 2008 Street Bob® $13,795.00 $7,499.00

    312608
    Pre-owned
    2008
    41528 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1GX4168K312608
    BLACK
  • FXBBS 2022 Street Bob® 114 $15,349.00 $13,495.00

    063613
    Pre-owned
    2022
    2090 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YYK10NB063613
    Redline Red

    The lightest-weight Softail equipped with a Milwaukee-Eight® 114 engine for a quick and nimble ride with power to spare. A perfect performance base for customization with 2-up seating, black steel laced wheels and dark finishes deliver no nonsense, Raw Bobber attitude.

  • FXBB 2025 Street Bob™ $17,199.00 $15,999.00

    033542
    Pre-owned
    2025
    2596 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ916SB033542
    Iron Horse Metallic w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBR 2024 Breakout™ 117 $22,499.00 $20,499.00

    049726
    Pre-owned
    2024
    3757 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YEZ16RB049726
    Vivid Black

    Dripping with chrome, the Harley-Davidson® Breakout 117 is a raked-out cruiser that packs Milwaukee-Eight® 117 V-Twin muscle.

  • 2012 FLHX103 $19,499.00 $12,999.00

    692812
    Pre-owned
    2012
    23538 mi
    HD
    Windy City Harley-Davidson®
    1HD1KBM15CB692812
    BIG BLUE PEARL
  • 2012 FLHX103 $19,499.00 $10,895.00

    653948
    Pre-owned
    2012
    18512 mi
    HD
    Windy City Harley-Davidson®
    1HD1KBM10CB653948
    BLACK
  • XL 1200X 2016 Forty-Eight® $11,199.00 $8,495.00

    442408
    Pre-owned
    2016
    8631 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1LC313GC442408
    Vivid Black

    The first time the world saw this gas tank was 1948. But the world has never seen that iconic tank sitting atop anything quite like this. The Forty-Eight® motorcycle has been reborn. Everything that was great about it has been cranked up to a more intense level. Better seat. Better suspension. New …

  • XG750 2015 Street™ 750 $7,499.00 $3,995.00

    502997
    Pre-owned
    2015
    349 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4NBB17FC502997
    Black Denim

    When the street is where you live, it starts to live in you. True of a rider. True of a motorcycle. The look of the Harley-Davidson Street™ 750 motorcycle comes from the street. Born out of the custom tradition of tearing down a motorcycle to its raw, minimal essence and letting the pure rebellion …

  • RH975 2023 Nightster™ $13,949.00 $9,995.00

    305553
    Pre-owned
    2023
    5637 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1ZH111PB305553
    Redline Red

    The 2023 Nightster® evolves the Sportster® legacy into a nimble handling and confidence inspiring ride.

  • RH975 2022 Nightster™ $13,499.00 $9,195.00

    320378
    Pre-owned
    2022
    6082 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1ZH110NB320378
    Vivid Black

    The Harley-Davidson® Nightster™ is the next chapter in the Harley-Davidson® Sportster® legacy – a leap forward in performance and design built on a foundation laid 65 years ago. An instrument of expression, the Nightster™ features the all-new  Revolution® Max 975T liquid-cooled V-Twin engine tuned …

  • FXBR 2024 Breakout™ 117 $23,149.00 $20,999.00

    044125
    Pre-owned
    2024
    51 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YEZ1XRB044125
    White Onyx Pearl

    Dripping with chrome, the Harley-Davidson® Breakout 117 is a raked-out cruiser that packs Milwaukee-Eight® 117 V-Twin muscle.

PRE-OWNED INVENTORY


Explore affordable pre-owned Harley-Davidson® models at Windy City Harley-Davidson® in Libertyville, IL

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