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Showing 25 - 36 of 467 results
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Showing 25 - 36 of 467 results
  • FLSTNI 2006 Softail® Deluxe $14,495.00

    040939
    Pre-owned
    2006
    14588 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1JDB196Y040939
    G WHT/COBALT W/PINSTRIPE
  • FLSTC 2009 Heritage Softail® Classic $12,999.00 $8,499.00

    065923
    Pre-owned
    2009
    15885 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1BW5189Y065923
    BLACK W/PINSTRIPE

    Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight …

  • FLHXSE 2016 CVO™ Street Glide® $36,999.00 $23,999.00

    954420
    Pre-owned
    2016
    53054 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1PXN12GB954420
    Black Licorice with Midnight Cobalt Flames

    Let’s say you want to ride into Bike Week with a full-on custom look that drops jaws and pops eyes all along Main Street. But you also like a machine that’s built tight and right with all the latest in refined technology and touring comfort. And let’s say you want it all built around 110 cubic …

  • 2019 Harley-Davidson® Ultra Limited Vivid Black $26,799.00 $20,499.00

    659367
    Pre-owned
    2019
    14412 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1KEF13KB659367
    Vivid Black
  • 2010 Harley-Davidson® Super Glide® Custom Vivid Black $14,999.00 $8,299.00

    321619
    Pre-owned
    2010
    24976 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1GV416AC321619
    Vivid Black
  • 2006 Cvo Ultra Classic Electra Glide EMERALD GREEN/GREEN W/PINSTRIPE $30,199.00 $9,999.00

    Pre-owned
    2006
    42030 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1PRE156Y952569
    EMERALD GREEN/GREEN W/PINSTRIPE
  • FLHXST 2022 Street Glide® ST $30,199.00 $22,995.00

    645978
    Pre-owned
    2022
    14153 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1ABL13NB645978
    Vivid Black

    Elevated pro-touring bagger performance and style for the rider who just can’t ever get enough. The Street Glide™ ST model pairs the muscular Milwaukee-Eight® 117 powertrain with tough West Coast styling influences and new dark-and-bronze finishes. Undiminished rider comfort and the iconic batwing …

  • FLHC 2018 Heritage Classic $19,949.00 $11,995.00

    073795
    Pre-owned
    2018
    16421 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YAJ19JC073795
    INDGRYDNM/BLKDM W/PINSTRIPE

    The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

  • 2011 Softail® Deluxe $17,864.00 $10,999.00

    031915
    Pre-owned
    2011
    11383 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1JD514BB031915
    BLACK W/PINSTRIPE

    One of the most confidence-inspiring Big Twins, the Softail® Deluxe features an extremely low seat with "collapsing sides," pull back handlebar and riser, and easy-reach, extended kickstand. The powerful, counter-balanced Twin Cam 96B™ and 6-Speed Cruise Drive® transmission are appreciated by many …

  • FLRT 2024 Freewheeler™ $32,199.00 $26,499.00

    854643
    Pre-owned
    2024
    2929 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1MCP12RB854643
    Alpine Green / Vivid Black

    The Harley-Davidson® Freewheeler delivers aggressive styling, enticing performance, and confident handling on three wheels.

  • FLHTK 2022 Ultra Limited $29,995.00 $23,499.00

    648811
    Pre-owned
    2022
    11846 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KEF11NB648811
    Vivid Black - Black Finish

    From its heated handgrips down to its Twin-Cooled™ Milwaukee-Eight® 114 engine, the Ultra Limited motorcycle helps you find your balance in its marriage of machinery and technology. Need your bike to express your dark side? Check out the new bold black finish that engulfs the entire bike, from its …

  • 2008 CVO Road King $24,999.00 $11,999.00

    960536
    Pre-owned
    2008
    50751 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1PG8148Y960536

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®!