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Showing 193 - 204 of 467 results
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Showing 193 - 204 of 467 results
  • FLHXS 2022 Street Glide® Special $29,379.00 $22,999.00

    609697
    Pre-owned
    2022
    6865 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRP12NB609697
    White Sand Pearl

    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.

  • FLHXS 2017 Street Glide® Special $23,699.00 $15,999.00

    680374
    Pre-owned
    2017
    14561 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRC10HB680374
    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 …

  • FLHX 2019 Street Glide® $21,289.00 $16,499.00

    629118
    Pre-owned
    2019
    4546 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KBC14KB629118
    Kinetic Green

    The mould for the factory hot rod bagger was cut the day the Street Glide® motorcycle rolled off the line. It’s spawned imitators, but none measure up. The look is backed up by the refined power of a Milwaukee-Eight® 107 (1747cc) engine. It combines with a fully adjustable rear suspension, …

  • FLHX 2021 Street Glide® $22,499.00 $16,499.00

    610388
    Pre-owned
    2021
    12724 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KBC10MB610388
    Vivid Black

    The icon you love to see and love to be seen on. Powered by a Milwaukee-Eight® 107 engine, the Street Glide® lives up to its name with a fully adjustable rear suspension and a responsive front end that let you hum smoothly along rolling highways and winding roads. Its hot-rod bagger style and …

  • FLHRCI 2002 Road King® Classic $17,595.00 $6,995.00

    701854
    Pre-owned
    2002
    17855 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1FRW332Y701854
    LUXURY BLUE/ICE W/STRIPES
  • FLFBS 2023 Fat Boy® 114 $20,399.00 $14,999.00

    047003
    Pre-owned
    2023
    15627 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YGK17PB047003
    Bright Billiard Blue

    The original fat custom icon. Now lighter than the previous generation Fat Boy 114, and slinging torque from a Milwaukee-Eight® 114. You’ll feel the difference the instant you crack the throttle.

  • FLHXSE 2016 CVO™ Street Glide® $26,799.00 $21,999.00

    956322
    Pre-owned
    2016
    12774 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1PXN11GB956322
    CRB CRY/PTM FLM

    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 …

  • RH975S 2024 Nightster™ Special $13,949.00 $10,999.00

    305263
    Pre-owned
    2024
    8021 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZF114RB305263
    Billiard Gray

    With modern function and traditional form, the Harley-Davidson® Nightster Special has a liquid-cooled V-twin engine and a classic Sportster® silhouette.

  • RH975 2025 Nightster™ $10,899.00 $9,999.00

    309602
    Pre-owned
    2025
    55 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    MLY1ZH119SS309602
    Vivid Black

    With classic Sportster® form and modern function, the nimble Nightster has a low center of gravity, rider-focused tech, and a high-revving, liquid-cooled Revolution® Max 975T V-twin engine.

  • RH975 2022 Nightster™ $13,899.00 $8,999.00

    311880
    Pre-owned
    2022
    2160 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZH116NB311880
    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 …

  • RH1250S 2023 Sportster® S $16,849.00 $13,999.00

    302243
    Pre-owned
    2023
    4033 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZC416PB302243
    Vivid Black

    A new chapter opens in H-D’s longest running family, powered by the all-new Revolution® Max 1250T. To call it the ultimate Sportster® is an understatement. Prepare for a level of power and performance that has surpassed all expectations.

  • 2015 FLSTFB103 $17,499.00 $10,999.00

    015303
    Pre-owned
    2015
    9880 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1JNV16FC015303
    BLACK

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®!