PRE-OWNED BLOWOUT SALE

Explore Quality Pre-Owned Motorcycles at Windy City Harley-Davidson® in Libertyville, IL

Discover exceptional value with our selection of pre-owned Harley-Davidson® motorcycles at Windy City Harley-Davidson®. Each bike is meticulously inspected to ensure reliability and performance, offering you the confidence to ride with peace of mind. Whether you're seeking a powerful cruiser or a nimble street bike, our inventory features a variety of models to suit every rider's preferences. Browse through our collection below and find your perfect ride today. Don't miss out—these deals won't last long!

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Showing 277 - 288 of 461 results
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Showing 277 - 288 of 461 results
  • FLTRXS 2016 Road Glide® Special
    $26,699.00 $16,999.00

    670850
    Pre-owned
    2016
    28000 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1KTM18GB670850
    Superior Blue

    Like the rock that diverts the mainstream, our frame-mounted Road Glide® Special motorcycle fairing splits the wind and conventional opinion alike. This is an exercise in how far you can take a motorcycle in terms of miles, attitude and function. You’ve got all the Project RUSHMORE features from …

  • 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 …

  • FLHXSE 2016 CVO™ Street Glide®
    $36,799.00 $22,999.00

    954104
    Pre-owned
    2016
    6215 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1PXN13GB954104
    BLK LIC/MDNTCBT W/PINSTRIPE

    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 …

  • flhtcutg 2016 Tri Glide® Ultra
    $25,999.00

    862086
    Pre-owned
    2016
    18562 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1MAL14GB862086
    Two-Tone Mysterious Red Sunglo/Velocity Red Sunglo

    The Tri Glide® Ultra model is everything you love about the Harley-Davidson® touring tradition, only more. You get every Project RUSHMORE feature and improvement applied to our three-wheel frame design. You also get the confidence of front to rear linked brakes. It all adds up to better miles and …

  • FLHXS 2015 Street Glide® Special

    692807
    Pre-owned
    2015
    53129 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRM15FB692807
    UNKNOWN

    This US bestseller has proven itself across everything the 50 states have thrown at it, and now it’s ready to take on the rest of the world. This is a machine that’s every bit as comfortable with a trip to the office as it is with a grand tour.Last year’s Project Rushmore gave it …

  • 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
    3785 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 …

  • XL 883N 2015 Iron 883™
    $9,899.00 $5,999.00

    434368
    Pre-owned
    2015
    12684 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD4LE219FC434368
    Black Denim

    The Iron 883™ motorcycle takes attitude to a dark place. Reflecting the style of riders who want a quality ride with no hassles, the blacked- out, back-alley bruiser is the “anti-chrome” Harley® model. The Iron 883 is for those who want their first taste of that ride-hard-and-put- up-wet lifestyle. …

  • Harley-Davidson® Iron 883™ 2015 XL 883N BLACK DENIM
    $9,249.00 $6,499.00

    426799
    Pre-owned
    2015
    4418 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD4LE217FC426799
    Black Denim

    The Iron 883™ motorcycle takes attitude to a dark place. Reflecting the style of riders who want a quality ride with no hassles, the blacked- out, back-alley bruiser is the “anti-chrome” Harley® model. The Iron 883 is for those who want their first taste of that ride-hard-and-put- up-wet lifestyle. …

  • Harley-Davidson® 1200 Custom 2015 XL1200C SUPERIOR BLUE W/ PINSTRIPE
    $10,909.00 $7,499.00

    402671
    Pre-owned
    2015
    5730 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1CT317FC402671
    Superior Blue

    Going up. This beauty retains all its original Sportster® credentials, but with a bigger 1200cc engine, a fatter front tyre on steel-laced wheel, a broader, flatter custom tank and a two-up seat. Bigger most certainly can be beautiful.1200 Custom Limited Edition AA tribute to North American Stock …

  • 2015 XL1200T
    $12,999.00 $7,999.00

    437995
    Pre-owned
    2015
    18886 mi
    HD
    Woodstock Harley-Davidson®
    1HD1LL31XFC437995
    AMBER-BLACK
  • Harley-Davidson® Heritage Softail® Classic 2015 FLSTC BLACK W/ PINSTRIPE
    $19,499.00 $10,195.00

    021830
    Pre-owned
    2015
    25479 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BWV13FB021830
    Vivid Black

    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 …