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Showing 13 - 24 of 466 results
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Showing 13 - 24 of 466 results
  • XL 1200X 2016 Forty-Eight®
    $11,199.00 $8,495.00

    442408
    Pre-owned
    2016
    8631 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1LC313GC442408
    Vivid Black

    The first time the world saw this gas tank was 1948. But the world has never seen that iconic tank sitting atop anything quite like this. The Forty-Eight® motorcycle has been reborn. Everything that was great about it has been cranked up to a more intense level. Better seat. Better suspension. New …

  • XL 1200NS 2018 Iron 1200™
    $9,999.00 $8,995.00

    426992
    Pre-owned
    2018
    6363 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1LP323JC426992
    Vivid Black

    If you’re looking for a clue on what the new Iron 1200™ is all about, look no further than the name. It all starts with the 1200cc Evolution® engine that gives you loads of famous Sportster® torque. It’s got a throwback look that goes right to the roots of Sportster, thanks to 70’s-inspired tank …

  • XL 1200N 2009 1200 Nightster®
    $9,899.00 $5,999.00

    408346
    Pre-owned
    2009
    15347 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    IHD1CZ3189K408346
    BLACK

    Ready to wheel its way through the alleyways and backstreets, the Nightster takes the Sportster legend in a dark direction with timeless styling. Black finishes cover wheel rims and hubs, forks and handlebars, hand and foot controls. Old school style fork gaiters and a bullet-hole belt guard …

  • XL 1200L 2008 Sportster® 1200 Low
    $10,485.00 $6,999.00

    414876
    Pre-owned
    2008
    21233 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1CX3188K414876
    CRIMSON RED
  • XG750 2015 Street™ 750
    $7,499.00 $3,995.00

    502997
    Pre-owned
    2015
    339 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4NBB17FC502997
    Black Denim

    When the street is where you live, it starts to live in you. True of a rider. True of a motorcycle. The look of the Harley-Davidson Street™ 750 motorcycle comes from the street. Born out of the custom tradition of tearing down a motorcycle to its raw, minimal essence and letting the pure rebellion …

  • XG500 2015 Street™ 500
    $7,194.00 $5,499.00

    503681
    Pre-owned
    2015
    3791 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4NAA12FC503681
    MYSTERIOUS RED

    When the street is where you live, it starts to live in you. True of a rider. True of a motorcycle. The look of the Harley-Davidson Street™ 500 motorcycle comes from the street. Born out of the custom tradition of tearing down a motorcycle to its raw, minimal essence and letting the pure rebellion …

  • Sportster 883 1986 GOLDEN BLACK PEARL
    $7,999.00 $3,999.00

    122172
    Pre-owned
    1986
    8018 mi
    Harley-Davidson®
    Starved Rock Harley-Davidson
    1HD4CAM17GY122172
    GOLDEN BLACK PEARL
  • RH975S 2025 Nightster™ Special
    $13,249.00 $11,999.00

    302308
    Pre-owned
    2025
    72 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    MLY1ZF111SS302308
    Whiskey Fire

    The Nightster Special marries iconic Sportster® design with modern, high-revving, liquid-cooled engine performance and rider-focused tech that keeps you connected on the road.

  • RH975S 2025 Nightster™ Special
    $14,799.00 $13,950.00

    S304826
    Pre-owned
    2025
    1621 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    MLY1ZF110SS304826
    Billiard Gray

    The Nightster Special marries iconic Sportster® design with modern, high-revving, liquid-cooled engine performance and rider-focused tech that keeps you connected on the road.

  • 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.

  • RH975S 2024 Nightster™ Special
    $13,799.00 $11,999.00

    308389
    Pre-owned
    2024
    449 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZF118RB308389
    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.

  • RH975S 2023 Nightster™ Special
    $15,199.00 $10,999.00

    308530
    Pre-owned
    2023
    52 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1ZF119PB308530
    BRT BILIARD BLU

    Harley-Davidson® introduces a new middle-weight contender that combines classic Sportster® silhouette with the sophisticated performance of the Revolution® Max 975T engine. Adding to the already successful mix of style, convenience and technology found in Nightster™, upgrades and new features on …