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Showing 85 - 96 of 467 results
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Showing 85 - 96 of 467 results
  • FXFB 2018 Fat Bob® $16,999.00 $11,995.00

    030296
    Pre-owned
    2018
    10493 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YKJ1XJC030296
    Black Denim

    Something this groundbreaking can only come from Harley-Davidson. The all-new Fat Bob®. Twenty-two pounds lighter, massive Milwaukee-Eight® engine power, asphalt-eating traction, a pothole-devouring suspension, agile cornering, and a take-no-prisoners look. You get a 2-1-2 upswept exhaust, a never-…

  • FXDB 2016 Street Bob® $13,699.00 $10,995.00

    302910
    Pre-owned
    2016
    6749 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1GXM19GC302910
    Olive Gold

    The original bobber fanatics invented the style you see here, and they had one rule: if it weighs you down, get rid of it. That’s the Street Bob® motorcycle in spades. Solo seat. Chopped rear fender. Mini-apes putting your fists in the wind. All it takes is a twist of the wrist to send whatever the …

  • FXBBS 2022 Street Bob® 114 $15,349.00 $12,995.00

    056888
    Pre-owned
    2022
    22200 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YYK14NB056888
    GAUNT GRY MTLIC

    The lightest-weight Softail equipped with a Milwaukee-Eight® 114 engine for a quick and nimble ride with power to spare. A perfect performance base for customization with 2-up seating, black steel laced wheels and dark finishes deliver no nonsense, Raw Bobber attitude.

  • FLTRX 2013 Road Glide® Custom $19,799.00 $12,495.00

    685440
    Pre-owned
    2013
    19133 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KHM18DB685440
    BLUE

    The Road Glide® Custom is a tough, low version of the shark-nose Harley-Davidson classic, with a big 18-inch front wheel, a 2-into-1 exhaust, and a smooth tail light assembly. This bagger rolls with swagger. The innovative Harley-Davidson® Touring chassis is based on a single-spar, rigid backbone …

  • FLHTK 2012 Electra Glide® Ultra Limited $23,799.00 $12,995.00

    689203
    Pre-owned
    2012
    27083 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KEM17CB689203
    EMBR RED/MERLOT W/ PINSTRIP

    The Electra Glide® Ultra Limited provides the next step for those looking to stand out and upgrade their ride. Redefining "fully-loaded," the Electra Glide Ultra Limited boasts the large, 1690 cc Twin Cam 103™ engine, anti-lock brakes, electronic cruise control, Smart Security System, unique two-…

  • FLHR 2013 Road King® $17,699.00 $10,995.00

    669275
    Pre-owned
    2013
    19188 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1FBM13DB669275
    MIDNIGHT PEARL W/ PINSTRIPE

    When the original Harley-Davidson® Road King® motorcycle was introduced in 1994, it didn't take long for it to obtain iconic status with heritage going back to the original 1965 Electra Glide® model. It may look like a timeless boulevard cruiser, but it is also a fully equipped, long-distance …

  • FLHR 2014 Road King® $19,054.00 $12,995.00

    666521
    Pre-owned
    2014
    36371 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1FBM18EB666521
    BIG BLUE/V BLK W/ PINSTRIPE

    The 2014 Road King® Classic takes the idea of Classic to the most modern place it's ever been. As part of Project RUSHMORE, it has been redesigned for 2014 to make the ride better than it's ever been. The bike is powered with a new rubber-mounted high output Twin Cam 103™ engine that gives you more …

  • XL 883N 2021 Iron 883™ $10,299.00 $8,499.00

    413492
    Pre-owned
    2021
    911 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4LE210MB413492
    Snake Venom

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

  • FLHR 2013 Road King® $22,249.00 $11,499.00

    B653023
    Pre-owned
    2013
    23110 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1FBM16DB653023
    BLACK

    When the original Harley-Davidson® Road King® motorcycle was introduced in 1994, it didn't take long for it to obtain iconic status with heritage going back to the original 1965 Electra Glide® model. It may look like a timeless boulevard cruiser, but it is also a fully equipped, long-distance …

  • FLTRXS 2019 Road Glide® Special $29,589.00 $21,499.00

    623939
    Pre-owned
    2019
    5757 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KTP13KB623939
    UNKNOWN

    The Road Glide® Special model gets a blacked-out Milwaukee-Eight® 114 (1868cc) engine standard this year. Which means our darkest, most road-devouring road machine goes to an even darker, more road-hungry place. You get the all-new big screen BOOM! ™ GTS infotainment system, premium Talon wheels, …

  • FXDBP 2008 Street Bob® $14,095.00 $7,499.00

    307811
    Pre-owned
    2008
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1GX4398K307811
    DARK BLUE DENIM
  • FLHRC 2007 Road King® Classic $17,695.00 $8,499.00

    701994
    Pre-owned
    2007
    17709 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1FR4177Y701994
    BLACK CHERRY W/PINSTRIPE

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®!