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Showing 169 - 180 of 467 results
  • 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.

  • FXBB 2020 Street Bob® $14,599.00 $12,999.00

    066784
    Pre-owned
    2020
    3983 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJJ11LB066784
    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 …

  • FXBB 2019 Street Bob® $14,549.00 $11,495.00

    066746
    Pre-owned
    2019
    2458 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJJ25KB066746
    Vivid Black

    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 …

  • FLTRK 2020 Road Glide® Limited $29,599.00 $20,999.00

    608125
    Pre-owned
    2020
    31800 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KZF19LB608125
    BRSLVDNM/BLKDNM W/PINSTRIPE
  • FLSTFB 2011 Fat Boy® Lo $16,299.00 $8,995.00

    018799
    Pre-owned
    2011
    34257 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1JN51XBB018799
    BLACK DENIM

    Building on the Fat Boy® legacy, the Fat Boy® Lo brought a darker, slammed appearance to the world of boulevard cruisers. From front to back, this custom cruiser shows attitude, with custom, black bullet hole wheels, a denim black frame, blacked-out covers and header shields, and satin chrome in …

  • FLSTC 2016 Heritage Softail® Classic $17,349.00 $12,495.00

    041206
    Pre-owned
    2016
    22295 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BWV31GB041206
    Superior Blue

    The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s only half of the equation for the rider of today. The hidden suspension gives you the authentic look without the bone-shaking ride of an old Hardtail. You get the comfort of cruise control for those long stretches of …

  • FLHXST 2023 Street Glide® ST $29,999.00 $23,995.00

    628316
    Pre-owned
    2023
    3179 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1ABL10PB628316
    Vivid Black

    Elevated pro-touring bagger performance and style for the rider who just can’t ever get enough. The Street Glide™ ST model pairs the muscular Milwaukee-Eight® 117 powertrain with tough West Coast styling influences and new dark-and-bronze finishes. Undiminished rider comfort and the iconic batwing …

  • FLHXSE 2017 CVO™ Street Glide® $37,799.00 $22,995.00

    954910
    Pre-owned
    2017
    37171 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1PXF18HB954910
    Starfire Black/Atomic Red with Contrast Chrome Aggressor Wheels

    The CVO Street Glide® is decked out fender to fender with custom details and our most powerful engine and sound system. The all-new black granite Milwaukee-Eight™ 114 engine is at the heart and when you unleash it at the light, hold on. The 6.5” BOOM!™ Stage II speakers are powered by two 300-watt …

  • FLHXS 2018 Street Glide® Special $25,999.00 $19,999.00

    657245
    Pre-owned
    2018
    11756 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRC19JB657245
    Vivid Black

    When it comes to hot rod baggers, the Street Glide® Special is way out front. You get the tire-smoking power of its blacked-out Milwaukee-Eight® 107 engine sitting at the heart of dark finishes that stretch from headlight to exhaust. A new 19-inch Talon front wheel and 18-inch rear wheel. Stretched …

  • FLHX 2015 Street Glide® $20,599.00 $13,495.00

    688521
    Pre-owned
    2015
    19103 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KBM11FB688521
    Charcoal Satin
  • FLHX 2025 Street Glide™ $30,649.00 $27,999.00

    615831
    Pre-owned
    2025
    1198 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB716SB615831
    Purple Abyss Denim - Black Finish

    After nearly two decades spent on the open road, the Street Glide® redefines touring with a liquid-cooled Milwaukee-Eight® 117 V-twin engine that puts out 126 ft-lb of torque, hand-adjustable rear shocks that smooth out the ride, and an easy-to-use touchscreen infotainment system that puts total …

  • FLHTKSE 2020 CVO™ Limited $44,039.00 $29,999.00

    952231
    Pre-owned
    2020
    20337 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1TEH13LB952231
    Moonlight Blue & Deep Sea Blue

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®!