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Showing 313 - 324 of 467 results
  • FXBB 2025 Street Bob™ $17,399.00 $15,999.00

    010288
    Pre-owned
    2025
    1035 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJ912SB010288
    Billiard Gray 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.

  • FLHR 2015 Road King® Classic $19,649.00 $12,999.00

    631957
    Pre-owned
    2015
    46164 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1FBM10FB631957
    Superior Blue

    As you can clearly see, our Road King® Classic owes its rocking looks to the golden decade of the 1950s. This ‘boulevard cruiser’ drips in chrome, leather and whitewalls, but naturally it also benefits from a wealth of today’s technology. Air-adjusted suspension, electronically linked ABS braking …

  • FLSTF 2009 Fat Boy® $16,544.00 $10,999.00

    033532
    Pre-owned
    2009
    26973 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BX5119Y033532
    BLACK

    One of the world’s most distinctive motorcycles, the FLSTF Fat Boy rolls with a size and stature second to none. The Fat Boy rides wide on a 200mm rear tyre hugged by a deep rear fender with a 17-inch front wheel and bright chrome fork nacelle. Unique premium components like bullet-hole disc …

  • XL 883N 2022 Iron 883™ $10,499.00 $8,999.00

    413256
    Pre-owned
    2022
    3113 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD4LE218NB413256
    Black Denim

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

  • FXSTD 2006 Softail Deuce $17,805.00 $11,999.00

    033252
    Pre-owned
    2006
    6199 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1JBB196Y033252
    COBALT/SILVER W/PINSTRIPE
  • FXST 2020 Softail Standard® $13,799.00 $12,999.00

    053232
    Pre-owned
    2020
    1121 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BVJ16LB053232
    Vivid Black

    The new Softail® Standard motorcycle offers the essential Harley-Davidson® cruiser experience - a lean Bobber profile steeped in attitude, classic Vivid Black paint highlighted with gleaming chrome wheels and polished finishes, the dynamic performance of the Harley-Davidson® Softail® chassis and …

  • Harley-Davidson® Street Glide® Special 2018 FLHXS LEGEND BLUE DNM $26,699.00 $16,999.00

    625936
    Pre-owned
    2018
    52063 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KYC15JB625936
    Legend Blue Denim

    When it comes to hot rod baggers, the Street Glide® Special is way out front. You get the tire-smoking power of its blacked-out Milwaukee-Eight® 107 engine sitting at the heart of dark finishes that stretch from headlight to exhaust. A new 19-inch Talon front wheel and 18-inch rear wheel. Stretched …

  • Harley-Davidson® Breakout® 2014 FXSB HCCHROMEFLAKE $19,899.00 $10,999.00

    B028539
    Pre-owned
    2014
    28984 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BFV12EB028539
    HCCHROMEFLAKE

    The 2014 Breakout® is a premium drag bike that mixes premium features, fit and finishes with a wide, muscular, stance and slammed, low-slung power profile inspired by classic Gasser dragsters of the 1950s and 1960s. It has a stretched, slammed custom style that's low, long and aggressive. Powered …

  • Harley-Davidson® Street Glide® Special 2021 FLHXS BLACK JACK METALLIC $28,499.00 $19,999.00

    676679
    Pre-owned
    2021
    15728 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRP17MB676679
    Black Jack Metallic

    The custom hot rod bagger look stops people in their tracks. Now powered up with the Milwaukee-Eight® 114 engine, you’ll leave them in your dust.

  • Harley-Davidson® Ultra Classic® Electra Glide® 2013 FLHTCU EMBR RED SUNGLO W/ PINSTRIP $23,039.00 $10,999.00

    669566
    Pre-owned
    2013
    43708 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1FCM16DB669566
    EMBR RED SUNGLO W/ PINSTRIP

    The Ultra Classic® Electra Glide® sets the standard for long-haul touring comfort and convenience. Though many imitators sought to duplicate it, the Ultra Classic Electra Glide stands tall as a benchmark for touring enthusiasts. A fourspeaker, 80-watt Harmon/Kardon® Advanced Audio System, one-piece,…

  • Harley-Davidson® Softail™ Standard 2024 FXST VIVID BLACK $16,999.00 $13,999.00

    038666
    Pre-owned
    2024
    3656 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1BVJ17RB038666
    Vivid Black

    A raw, stripped-down, bobber-style bike, the Harley-Davidson® Softail Standard is an ideal blank canvas for customization.

  • Harley-Davidson® Softail Slim® 2013 FLS BLACK $17,049.00 $13,999.00

    015481
    Pre-owned
    2013
    9913 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1JRV15DB015481
    BLACK

    Pare down a Harley-Davidson® Softail® motorcycle to its essential elements and you have the Slim. From its trimmed front fender to its narrow rear end, Slim is a no-nonsense, back-to-basics motorcycle. Call it stripped. Call it old school. Call it lean and mean. What's left is the elemental Softail …

PRE-OWNED INVENTORY


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

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