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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Chicago Harley-Davidson®

Illinois Harley-Davidson®

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Windy City Harley-Davidson®

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FLHXS 2018 Street Glide® Special
$25,999.00 $20,999.00

677538

Pre-owned

2018

23653 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KRC13JB677538

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 …

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2018 Harley-Davidson® CVO™ Street Glide® Dark Alloy & Black Denim
$39,999.00 $24,999.00

958014

Pre-owned

2018

22193 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1PXL18JB958014

Dark Alloy & Black Denim

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2018 Harley-Davidson® Tri Glide® Ultra Twisted Cherry/Silver Fortune
$36,669.00 $29,999.00

852934

Pre-owned

2018

7804 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1MAD17JB852934

Twisted Cherry/Silver Fortune

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FLHTCUTG 2017 Tri Glide® Ultra

860258

Pre-owned

2017

8895 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1MAD18HB860258

SUPERIOR BLUE W/PINSTRIPE

The Tri Glide® Ultra is everything you love about the Ultra Limited, only on three wheels. You get every feature and improvement starting with the power of the all-new Twin-Cooled™ Milwaukee-Eight™ 107 engine. Other touring features include a 4-speaker, premium BOOM!™ Box 6.5 …

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Harley-Davidson® Harley-Davidson Street® 750 2017 XG750 BLACK
$8,049.00 $5,999.00

507007

Pre-owned

2017

680 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD4NBB19HC507007

Black Denim

This is a machine built to let you shred traffic in plenty of infinitely customizable Harley-Davidson® Dark CustomTM style. Liquid-cooled engine. Quick handling. A suspension tuned for rough pavement. Fire up the blacked out engine, send some sound out the blacked out pipes, and get behind the café …

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FXDF 2017 Fat Bob®
$16,499.00 $9,999.00

308538

Pre-owned

2017

9088 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1GYM12HC308538

Crushed Ice Denim

Subtle is not the word that comes to mind when describing the Fat Bob®. Tommy Gun exhaust. A unique dual headlight and custom LED tail light. Fat rubber rolling on machined disc wheels. And performance that lets you get down to business with the Twin Cam 103™ engine and dual disc brakes. The look …

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2017 Harley-Davidson® Street Bob® Black Denim
$16,699.00 $11,499.00

318556

Pre-owned

2017

20218 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1GXM17HC318556

Black Denim

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2017 Harley-Davidson® Low Rider® Two-Tone Billet Silver/Vivid Black
$15,999.00 $11,799.00

306001

Pre-owned

2017

9925 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1GNM16HC306001

Two-Tone Billet Silver/Vivid Black

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Harley-Davidson® Heritage Softail® Classic 2017 FLSTC BLACK
$11,999.00

034478

Pre-owned

2017

24500 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1BWV1XHB034478

Two-Tone Black Hills Gold/Black Quartz

The Heritage Softail® Classic is rich with the nostalgia of days gone by, but the hidden suspension gives you the authentic look of a hardtail without the bone-shaking ride. You get the comfort of standard cruise control and a low center of gravity, plus standard ABS, and a High Output Twin Cam …

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Harley-Davidson® Ultra Limited 2017 FLHTK BLACK QUARTZ W/PINSTRIPE
$25,899.00 $14,499.00

675623

Pre-owned

2017

47091 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KED14HB675623

Two-Tone Black Hills Gold/Black Quartz

If you’re the kind who wants it all, the Ultra Limited gives it to you. From the powerful all-new Twin-Cooled™ Milwaukee-Eight™ 107 engine, right down to the heated handgrips. The unmistakable Batwing fairing and Splitstream air vent mean optimal air flow and reduced head buffeting. Premium BOOM!™ …

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FLHTCU 2017 Electra Glide® Ultra Classic®
$14,999.00

645197

Pre-owned

2017

20480 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1FCC13HB645197

BIL SLVR/V BLK W/PINSTRIPE

Get in the two-up Electra Glide® seat and there are absolutely no limits to how far you can go or how good it’s all going to feel.With each passing mile it only gets better.From the day the first Electra Glide® motorcycle crossed the country in 1965, it’s had a singular mission. Make the ride a …

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FLHXS 2017 Street Glide® Special
$24,299.00 $15,999.00

657933

Pre-owned

2017

7032 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRC15HB657933

Black Denim

The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

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