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Showing 49 - 60 of 467 results
  • FXBR 2025 Breakout™ $23,299.00 $21,999.00

    022585
    Pre-owned
    2025
    9784 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YE913SB022585
    Vivid Black

    With a wide rear tire, bobtail rear fender, long rake, straight handlebars, and a 21-inch front wheel, the Breakout marries classic chopper style with the performance of a Milwaukee-Eight® 117 Custom powertrain.

  • FLHC 2018 Heritage Classic $19,949.00 $13,999.00

    029384
    Pre-owned
    2018
    24807 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YAJ1XJC029384
    Silver Fortune

    The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

  • FLTRT 2023 Road Glide® 3 $33,199.00 $31,999.00

    859407
    Pre-owned
    2023
    131 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1MFP16PB859407
    BRT BILIARD BLU

    The 2023 Road Glide® 3 combines the soul of a Road Glide® with all the benefits of three-wheels

  • RH975 2024 Nightster™ $12,199.00 $10,999.00

    302276
    Pre-owned
    2024
    5019 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1ZH114RB302276
    Billiard Gray

    Designed to inspire riders of all skill levels, the Harley-Davidson® Nightster introduces a new narrative in the Sportster® story.

  • FLHXSE 2016 CVO™ Street Glide® $36,999.00 $22,999.00

    950336
    Pre-owned
    2016
    18710 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1PXN14GB950336
    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 …

  • FLHXSE 2019 CVO™ Street Glide® $41,089.00 $28,999.00

    951897
    Pre-owned
    2019
    4757 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1PXL10KB951897
    Black Forest

    There’s the best, and there’s all the rest. When it comes to custom touring, the CVO™ Street Glide® model is as far up the ladder as you can go. You get the power of the Milwaukee-Eight® 117 (1923cc) V-Twin engine, red rocker covers, premium Talon wheels and custom controls, all-new BOOM!™ Box GTS …

  • FLHTCUTG 2013 Tri Glide™ Ultra Classic® $32,549.00 $23,999.00

    DB852129
    Pre-owned
    2013
    32990 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1MAM28DB852129
    BROWN\BLACK

    The Tri Glide™ Ultra Classic® is a full-feature, factory motorcycle built to confidently chase the horizon with long-haul comfort and freedom on three wheels. The Harley-Davidson® Trike platform brings original-equipment design, quality and service to the three-wheel motorcycle segment. Trike …

  • FLHTCUTG 2025 Tri Glide® Ultra $38,199.00 $35,999.00

    854872
    Pre-owned
    2025
    3 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1MAF11SB854872
    Mystic Shift - Black Finish

    A full-dresser, long-haul trike with room for cargo, the Tri Glide Ultra is available in classic chrome or all-new dark finishes. Load up the trunk and King Tour-Pak® luggage carrier with amenities for days on the road and enjoy the comfort and confidence of three-wheels on your greatest adventures.

  • FLHX 2024 Street Glide® $26,999.00 $24,999.00

    618686
    Pre-owned
    2024
    2553 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KB712RB618686
    Billiard Gray

    The iconic batwing fairing takes on new life with a sculpted silhouette, fully integrated LED lighting, and a split-stream vent opening. Using computational fluid dynamics (CFD), the Street Glide fairing has been designed to optimize aerodynamic efficiency and enhance rider comfort.

  • FLTRK 2022 Road Glide® Limited $32,249.00 $23,999.00

    644363
    Pre-owned
    2022
    4839 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KZF13NB644363
    Mineral Green Metallic

    A fully loaded Grand Touring machine with 114 cubic inches of power and new premium finishes. Enjoy the ride to the fullest.

  • FLSTC 2015 Heritage Softail® Classic $18,999.00 $10,999.00

    016453
    Pre-owned
    2015
    25427 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BWV17FB016453
    Morocco Gold Pearl

    The perfect marriage of styling that dates back 80-odd years, and technology that’s bang up to date. With its classy whitewalls, full fenders and leather-studded saddlebags, the Heritage gives you 40s styling in spades.This year we’ve improved the braking system to give it an even better feel with …

  • FLRT 2018 Freewheeler® $26,449.00 $19,999.00

    859422
    Pre-owned
    2018
    6730 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1MCC18JB859422
    Vivid Black

    The Freewheeler® model puts stripped-down custom style into an easy handling frame that lets you roll with the confidence three wheels gives to a rider. You get classic cruiser lines and styling details, like bobtail rear fenders, slash cut pipes, a chrome headlight nacelle, 12-inch mini-ape …

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®!