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®

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Windy City Harley-Davidson®

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Harley-Davidson® CVO™ Road Glide® 2019 FLTRXSE REDPEP/MAG GRAY W/PINSTRIPE
$50,999.00 $40,999.00

953547

Pre-owned

2019

17000 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1TCL1XKB953547

Red Pepper & Magnetic Gray with Black Hole

For those who want to cut the widest swath possible, we’re proud to offer the CVO™ Road Glide®. From the tip of its shark-nose fairing and new Fang spoiler to its LED rear light, this machine is loaded with the kind of custom details that will turn heads and drop jaws wherever it goes. You get …

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FLHTK 2018 Ultra Limited

662718

Pre-owned

2018

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KED18JB662718

BLACK

If you’re the kind who wants it all, the Ultra Limited model gives it to you. From the powerful Twin-Cooled™ Milwaukee-Eight®107 engine right down to the heated hand grips. The unmistakable Batwing fairing and splitstream air vent mean optimal air flow and reduced head buffeting. …

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2018 Harley-Davidson® Iron 883™ Black Denim
$9,999.00 $6,999.00

423344

Pre-owned

2018

13668 mi

Harley-Davidson®

1HD4LE215JC423344

Black Denim

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XL1200C 2018 1200 Custom
$11,549.00 $7,999.00

410016

Pre-owned

2018

8097 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1CT313JC410016

INDGRYDNM/BLKDM W/PINSTRIPE

There’s a reason the word “custom” is in the name of the Sportster® 1200 Custom model. It’s the bike for those who put a premium on making a personal statement. Now the attitude gets pushed to a new black-and-chrome edge. The 1200 Evolution® V-Twin engine features black rockers, a new black chrome …

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Harley-Davidson® Iron 883™ 2018 XL 883N BNVL SALT DENIM
$9,549.00 $8,495.00

421090

Pre-owned

2018

2011 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD4LE211JC421090

Bonneville Salt Denim

Feel the purity of two wheels, a handle bar and an engine. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, the Iron 883™ model has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with …

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FXLR 2018 Low Rider®
$15,399.00 $10,499.00

081069

Pre-owned

2018

18260 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YNJ1XJC081069

Vivid Black

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

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FXLR 2018 Low Rider®
$18,995.00 $10,995.00

070492

Pre-owned

2018

9000 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YNJ1XJC070492

Wicked Red

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

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Harley-Davidson® Fat Bob® 114 2018 FXFBS INDSTRL GRY DNM
$19,299.00 $11,499.00

034612

Pre-owned

2018

3993 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YLK18JC034612

INDSTRL GRY DNM

You can take the aggressive, futuristic look and adrenaline-pumping ride of the Fat Bob® as far as you want to go with Harley-Davidson® Genuine Motor Accessories and the Screamin’ Eagle® Milwaukee-Eight® 114 engine with Stage I upgrade.

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FLS 2018 Softail Slim®
$16,299.00 $11,999.00

069597

Pre-owned

2018

14728 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YDJ15JC069597

BLUE

The idea behind bobbers has always been to strip down and soup up the bike for a more exciting ride. The all-new Softail Slim® takes that idea to the edge. It’s 35 pounds lighter than last year’s model. It’s got more power, more lean angle, and a redesigned front and rear suspension. So you can put …

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FXFBS 2018 Fat Bob® 114
$16,699.00 $11,999.00

038459

Pre-owned

2018

10641 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YLK12JC038459

Bonneville Salt Denim

You can take the aggressive, futuristic look and adrenaline-pumping ride of the Fat Bob® as far as you want to go with Harley-Davidson® Genuine Motor Accessories and the Screamin’ Eagle® Milwaukee-Eight® 114 engine with Stage I upgrade.

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FLSB 2018 Sport Glide™
$18,799.00 $12,999.00

035204

Pre-owned

2018

24527 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YMJ29JC035204

Vivid Black

Devour endless miles with some room for gear. Or strip it down and carve city streets. The all-new Sport Glide™ is locked and loaded for whatever, whenever. You’ll be riding on the most advanced frame we’ve ever offered — the completely redesigned Softail® Inverted front forks and a fully …

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FLS 2018 Softail Slim®
$16,299.00 $13,999.00

C079175

Pre-owned

2018

6026 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YDJ17JC079175

Black Denim

The idea behind bobbers has always been to strip down and soup up the bike for a more exciting ride. The all-new Softail Slim® takes that idea to the edge. It’s 35 pounds lighter than last year’s model. It’s got more power, more lean angle, and a redesigned front and rear suspension. So you can put …

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