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Showing 301 - 312 of 493 results
  • FLHTCU 2017 Electra Glide® Ultra Classic® $14,999.00

    645197
    Pre-owned
    2017
    20480 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1FCC13HB645197
    BIL SLVR/V BLK W/PINSTRIPE

    Get in the two-up Electra Glide® seat and there are absolutely no limits to how far you can go or how good it’s all going to feel.With each passing mile it only gets better.From the day the first Electra Glide® motorcycle crossed the country in 1965, it’s had a singular mission. Make the ride a …

  • 2005 Harley-Davidson® Electra Glide® Ultra Classic® Vivid Black $13,899.00 $7,999.00

    680816
    Pre-owned
    2005
    46342 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD1FCW195Y680816
    Vivid Black
  • FXBB 2025 Street Bob™ $17,399.00 $16,999.00

    SB018364
    Pre-owned
    2025
    98 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJ91XSB018364
    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.

  • FXBB 2020 Street Bob® $15,549.00 $12,999.00

    LB031329
    Pre-owned
    2020
    14923 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJJ10LB031329
    BRACUDA SLV DNM W/PINSTRIPE

    The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

  • FXST 2022 Softail Standard® $14,149.00 $13,999.00

    NB038240
    Pre-owned
    2022
    2227 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BVJ13NB038240
    Vivid Black

    A stripped-down, souped-up, bobber with a post WWII era look. You get the power and soul-satisfying  sound of the Milwaukee-Eight® 107 V-Twin to take you into the future. Fast.

  • FXFBS 2022 Fat Bob® 114 $19,799.00 $15,999.00

    NB051876
    Pre-owned
    2022
    11613 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YLK11NB051876
    Vivid Black

    The Fat Bob® is all Harley-Davidson, but at the same time, it’s unlike any Harley® motorcycle that ever existed before. From the modern, aggressive look of its 2-1-2 upswept exhaust and tarmac-devouring fat tyres to the massive torque of the Milwaukee-Eight® engine to the ride of the Softail® frame,…

  • FLSTC 2014 Heritage Softail® Classic $19,479.00 $10,999.00

    EB036949
    Pre-owned
    2014
    9626 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BWV16EB036949
    BIG BLUE/V BLK W/ PINSTRIPE

    The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …

  • FLSTC 2009 Heritage Softail® Classic $18,854.00 $9,499.00

    Y052293
    Pre-owned
    2009
    32821 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BW5129Y052293
    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 …

  • FLFBS 2020 Fat Boy® 114 $21,949.00 $16,999.00

    LB012674
    Pre-owned
    2020
    7588 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YGK18LB012674
    Stiletto Red

    The name may be Fat Boy®, but the look is all muscle. This is the icon, riding on a 240mm rear tyre, 160mm front tyre and solid disc wheels. You get satin chrome finishes and signature LED lighting. This version is 14 kilograms lighter than the previous generation Fat Boy models, and its slinging …

  • FXDI35 2006 35th Anniversary Super Glide $16,795.00 $12,999.00

    6306683
    Pre-owned
    2006
    8233 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1GW1176K306683
    GLACIER WHITE
  • FLSTN 2009 Softail® Deluxe $18,299.00 $11,999.00

    055682
    Pre-owned
    2009
    12679 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1JD5179Y055682
    LT/DK ROOT BEER
  • FLSTN 2016 Softail® Deluxe $19,949.00 $14,999.00

    GB041349
    Pre-owned
    2016
    7342 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1JDV14GB041349
    Two-Tone Mysterious Red Sunglo/Velocity Red Sunglo

    There aren’t that many things left in this world that make a hard-working man or woman feel truly deluxe. This motorcycle is one of them. Roll into town and you can feel the eyes on the chrome and laced wheels, wrapped in whitewall tires. The full-skirted metal fenders. The big chromed headlamp and …

PRE-OWNED INVENTORY


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

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