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Showing 181 - 192 of 467 results
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Showing 181 - 192 of 467 results
  • FLHX 2008 Street Glide® $19,125.00 $9,999.00

    689280
    Pre-owned
    2008
    30953 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB41X8Y689280
    DARK BLUE PEARL
  • FLHTK 2014 Electra Glide® Ultra Limited $25,899.00 $12,995.00

    665291
    Pre-owned
    2014
    11063 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KEL13EB665291
    MYS RED/CAYENNE W/ PINSTRIP

    The 2014 Ultra Limited® is a premium touring bike full of authentic Harley-Davidson® grand American touring style. As part of Project RUSHMORE, it has been redesigned for 2014 and features a new twin-cooled high output Twin Cam 103™ engine with more low-end torque and passing power and is combined …

  • FLHRXS 2024 Road King™ Special $24,999.00 $23,995.00

    664074
    Pre-owned
    2024
    1716 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KVP11RB664074
    Vivid Black

    A majestic bagger with impressive power, the Harley-Davidson® Road King Special has a uniquely commanding presence that makes you feel like road royalty.

  • FLFBS 2024 Fat Boy™ 114 $21,999.00 $18,999.00

    017290
    Pre-owned
    2024
    1703 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YGK13RB017290
    Red Rock

    The original fat custom icon. Loved since day one, the Harley-Davidson® Fat Boy 114 stands out with bright chrome and bold finishes.

  • XL 883N 2021 Iron 883™ $9,499.00 $7,999.00

    408221
    Pre-owned
    2021
    815 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4LE21XMB408221
    Black Denim

    An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look.

  • 2012 FLHX103 $20,699.00 $13,999.00

    680117
    Pre-owned
    2012
    33394 mi
    HD
    Chicago Harley-Davidson®
    1HD1KBM14CB680117
    EMBR RED SUNGLO
  • 2012 FLHR103 $18,279.00 $10,999.00

    691952
    Pre-owned
    2012
    9925 mi
    HD
    Chicago Harley-Davidson®
    1HD1FBM1XCB691952
    BLACK W/ PINSTRIPE
  • FXBBS 2022 Street Bob® 114 $16,749.00 $11,999.00

    NB050844
    Pre-owned
    2022
    1609 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YYK19NB050844
    Vivid Black

    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.

  • FLTRX 2019 Road Glide® $21,589.00 $16,999.00

    668087
    Pre-owned
    2019
    6359 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KHC11KB668087
    Vivid Black

    The menacing dual Daymaker™ Reflector LED headlamps in the Road Glide® motorcycle’s shark-nose fairing are a familiar sight on the highway. It’s the machine of choice for hard-charging riders. You get Milwaukee-Eight® 107 (1745cc) power, easily adjustable emulsion rear suspesion and responsive …

  • FLSTF 2007 Fat Boy® $17,095.00 $8,999.00

    035936
    Pre-owned
    2007
    24130 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BX5167Y035936
    RED PEARL
  • FXDC 2013 Super Glide® Custom $13,799.00 $8,999.00

    322423
    Pre-owned
    2013
    5529 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1GV41XDC322423
    CHRM YELLOW PRL W/ PINSTRIP

    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 …

  • FLHXS 2017 Street Glide® Special $24,299.00 $15,999.00

    657933
    Pre-owned
    2017
    7033 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRC15HB657933
    Black Denim

    The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

PRE-OWNED INVENTORY


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

Shop our entire selection of used Harley-Davidson® motorcycles for sale at Windy City Harley-Davidson®!