Harley-Davidson® Motorcycles For Sale in Chicago, IL & Milwaukee, WI
Windy City Motorcycle Company Inventory
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Quick Look 2016 Harley-Davidson® XL883N - Sportster® Iron 883™
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U432311IL -
Vin
1HD4LE211GC432311 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
3356 -
Family
Sportster®
2016 Harley-Davidson® Sportster® Iron 883™ Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street. A great leap forward in the dark arts. It was one of the early Dark Custom™ motorcycles. A dark pioneer of raw, blacked-out, stripped-down custom aggression. So the ques...
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Quick Look 2015 Harley-Davidson® XL883N - Sportster® Iron 883™
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U424176IL -
Vin
1HD4LE215FC424176 -
Vehicle Type
Motorcycle / Scooter -
Category
Standard -
Odometer
9513 -
Color
WHITE -
Family
Sportster®
2015 Harley-Davidson® Sportster® Iron 883™ This blacked-out bruiser is a raw, aggressive throwback. No apologies—just an authentic ride. The 2015 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom bobber. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tank, every pi...
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Quick Look 2006 Harley-Davidson® FLHTCUI - Ultra Classic® Electra Glide®
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Condition
Pre-owned -
Location
West Bend Harley-Davidson -
Stock Number
U655956WB -
Vin
1HD1FCW186Y655956 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
62954 -
Color
BLK -
Family
Touring
2006 Harley-Davidson® Ultra Classic® Electra Glide® The Ultra Classic® Electra Glide®. Down to the EFI Twin Cam 88® core, it’s everything you expect a Harley® road machine to be. Powerful. Refined. Legendary. Then it goes further in the ways of creature comforts. Comfort-stitched saddle with wraparound passenger backrest. Spacious hardbags and a r...
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Quick Look 2020 Harley-Davidson® XL883N - Sportster® Iron 883™
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Condition
Certified Pre-Owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U427805-MKE -
Vin
1HD4LE211LB427805 -
Vehicle Type
Motorcycle / Scooter -
Category
Sportster -
Odometer
10457 -
Color
BLACK -
Family
Sportster®
2020 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Features may include: Blacked-Out Look It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with ...
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Quick Look 2016 Harley-Davidson® XG750 - Street® 750
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Condition
Pre-owned -
Location
Woodstock Harley Davidson -
Stock Number
U501247WS -
Vin
1HD4NBB11GC501247 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
11690 -
Color
BLACK -
Family
Street™
2016 Harley-Davidson® Street® 750 Beneath the Dark Custom™ styling lurks a liquid-cooled 750cc Revolution X™ V-Twin engine. Traffic has never been beaten harder. Last year, we unleashed a new form of rebellion on the urban grid. The Harley-Davidson Street® 750 motorcycle. This is a machine built to let you shred traffic in plenty of infinitely cus...
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Quick Look 2006 Harley-Davidson® FXDI - Dyna® Super Glide
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Condition
Pre-owned -
Location
Fox River Harley-Davidson -
Stock Number
U329022FR -
Vin
1HD1GM1166K329022 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
14884 -
Color
RED -
Family
Dyna®
2006 Harley-Davidson® Dyna® Super Glide If your idea of living large is as simple as a long stretch of asphalt and a Big Twin rumbling beneath your seat, then look no further than the Super Glide.® Just as with all Dyna® models, it’s redesigned for 2006. The minimalist styling gets beefed up with 49mm forks. There’s a new solo seat. New 160mm rear...
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Quick Look 2020 Harley-Davidson® XG750A - Street Rod®
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U505004DNS -
Vin
1HD4NCG18LB505004 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
73 -
Color
BLACK -
Family
Street®
2020 Harley-Davidson® Street Rod® GET A LITTLE ADRENALINE SURGING THROUGH YOUR SOUL Turn city streets into a thrill ride. Redlines at 9000 rpm, and carves corners with up to 40 degrees of traffic-weaving lean angle. Features may include: High Output Revolution X™ 750 Engine With a blacked-out finish, the High Output Revolution X™ engine features a...
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Quick Look 2016 Harley-Davidson® XG750 - Street® 750
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Condition
Pre-owned -
Location
Triumph Detroit -
Stock Number
U500110TD -
Vin
1HD4NBB12GC500110 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
3657 -
Color
BLACK -
Family
Street™
2016 Harley-Davidson® Street® 750 Beneath the Dark Custom™ styling lurks a liquid-cooled 750cc Revolution X™ V-Twin engine. Traffic has never been beaten harder. Last year, we unleashed a new form of rebellion on the urban grid. The Harley-Davidson Street® 750 motorcycle. This is a machine built to let you shred traffic in plenty of infinitely cus...
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Quick Look 2014 Harley-Davidson® XL883N - Sportster® Iron 883™
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U423204IL -
Vin
1HD4LE213EC423204 -
Vehicle Type
Motorcycle / Scooter -
Category
Standard -
Odometer
1855 -
Family
Sportster®
2014 Harley-Davidson® Sportster® Iron 883™ This blacked-out bruiser is a raw, aggressive throwback. No chrome, no apologies—just an authentic ride. The 2014 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom bobber. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tan...
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Quick Look 2018 Harley-Davidson® XG750A - Street Rod™
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U509766IL -
Vin
1HD4NCG12JC509766 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
921 -
Family
Street®
2018 Harley-Davidson® Street Rod™ If you’re going to hit it, hit it hard. The all-new Street Rod™ motorcycle is built to take you to the edge. Features may include: New High Output Revolution X™ 750 Engine With a blacked-out finish, the High Output Revolution X™ engine features a dual throttle body, cylinder heads, enhanced intake ports and cams, ...
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Quick Look 2009 Harley-Davidson® XL1200L - Sportster® 1200 Low
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U405458IL -
Vin
1HD1CX3199K405458 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
28411 -
Family
Sportster®
2009 Harley-Davidson® Sportster® 1200 Low Offering a preferred blend of performance, agility and ergonomics, the Sportster® 1200 Low adds a recalibrated suspension and tire-hugging front fender for 2009. Powered by a fuel-injected 1200cc Evolution V-Twin™ engine, the 1200 Low also features a pull-back handlebar, a low 26.3-inch seat height, and a ...
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Quick Look 2006 Harley-Davidson® VRSCR - Street Rod™
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Condition
Pre-owned -
Location
Illinois Harley-Davidson -
Stock Number
U801011IL -
Vin
1HD1HCZ496K801011 -
Vehicle Type
Motorcycle / Scooter -
Category
Sport -
Odometer
22957 -
Color
ORANGE/SILVER -
Family
V-Rod®
2006 Harley-Davidson® Street Rod™ A high-performance roadster, the new VRSCR Street ™ combines an upright seating position, a 40-degree lean angle and retuned suspension to create a motorcycle that marries custom styling with a new level of cornering agility. Mid-mount foot controls, shorter handlebar risers and a taller seat move the rider forwar...
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Quick Look 2014 Harley-Davidson® XL883N - Sportster® Iron 883™
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Condition
Pre-owned -
Location
Chicago Harley-Davidson -
Stock Number
U446128 -
Vin
1HD4LE217EC446128 -
Vehicle Type
Motorcycle / Scooter -
Category
Standard -
Odometer
8011 -
Color
BLACK DENIM -
Family
Sportster®
2014 Harley-Davidson® Sportster® Iron 883™ This blacked-out bruiser is a raw, aggressive throwback. No chrome, no apologies—just an authentic ride. The 2014 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom bobber. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tan...
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Quick Look 2008 Harley-Davidson® XL1200L - Sportster® 1200 Low
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Condition
Pre-owned -
Location
Fox River Harley-Davidson -
Stock Number
U457704FR -
Vin
1HD1CX3178K457704 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
16567 -
Family
Sportster®
2008 Harley-Davidson® Sportster® 1200 Low The 1200 Low offers all of the performance of a fuel-injected 1200cc Evolution™ V-Twin™, with pull-back handlebar and a low 26.3 seat height for comfortable ergonomics and a 4.5-gallon fuel tank for increased range. Black 13-spoke Cast Aluminum 19-inch front wheel is only available on this Sportster model....
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Quick Look 2006 Harley-Davidson® XL883C - Sportster® 883® Custom
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Condition
Pre-owned -
Location
Fox River Harley-Davidson -
Stock Number
U434997FR -
Vin
1HD4CJM126K434997 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
43320 -
Color
BLUE -
Family
Sportster®
2006 Harley-Davidson® Sportster® 883 Custom The only thing better than a street bike is a custom street bike, like the Sportster® 883 Custom. Harley-Davidson® begins by giving it the smooth, rubber-mounted Evolution engine and 4.5-gallon tank.
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Quick Look 2018 Harley-Davidson® XG500 - Street® 500
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Condition
Pre-owned -
Location
Wild Fire Harley-Davidson -
Stock Number
U510171WF -
Vin
1HD4NAA12JC510171 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
1842 -
Color
BLACK -
Family
Street®
2018 Harley-Davidson® Street® 500 Take on the urban grid with 500cc of easy-handling, blacked-out Harley-Davidson® Dark Custom style. Features may include: 500cc Liquid-Cooled Revolution X™ Engine The blacked-out, liquid-cooled V-Twin engine is built to conquer the hot and heavy traffic of urban streets. You can count on smooth response to the pro...
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