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XL 1200X 2016 Forty-Eight®
$11,199.00 $8,495.00- 442408
- Pre-owned
- 2016
- 8631 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1LC313GC442408
- Vivid Black
The first time the world saw this gas tank was 1948. But the world has never seen that iconic tank sitting atop anything quite like this. The Forty-Eight® motorcycle has been reborn. Everything that was great about it has been cranked up to a more intense level. Better seat. Better suspension. New …
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XL 1200NS 2018 Iron 1200™
$9,999.00 $8,995.00- 426992
- Pre-owned
- 2018
- 6363 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1LP323JC426992
- Vivid Black
If you’re looking for a clue on what the new Iron 1200™ is all about, look no further than the name. It all starts with the 1200cc Evolution® engine that gives you loads of famous Sportster® torque. It’s got a throwback look that goes right to the roots of Sportster, thanks to 70’s-inspired tank …
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XL 1200N 2009 1200 Nightster®
$9,899.00 $5,999.00- 408346
- Pre-owned
- 2009
- 15347 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- IHD1CZ3189K408346
- BLACK
Ready to wheel its way through the alleyways and backstreets, the Nightster takes the Sportster legend in a dark direction with timeless styling. Black finishes cover wheel rims and hubs, forks and handlebars, hand and foot controls. Old school style fork gaiters and a bullet-hole belt guard …
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XL 1200L 2008 Sportster® 1200 Low
$10,485.00 $6,999.00- 414876
- Pre-owned
- 2008
- 21233 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1CX3188K414876
- CRIMSON RED
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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 …
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XG500 2015 Street™ 500
$7,194.00 $5,499.00- 503681
- Pre-owned
- 2015
- 3791 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 …
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Sportster 883 1986 GOLDEN BLACK PEARL
$7,999.00 $3,999.00- 122172
- Pre-owned
- 1986
- 8018 mi
- Harley-Davidson®
- Starved Rock Harley-Davidson
- 1HD4CAM17GY122172
- GOLDEN BLACK PEARL
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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.
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RH975S 2025 Nightster™ Special
$14,799.00 $13,950.00- S304826
- Pre-owned
- 2025
- 1621 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- MLY1ZF110SS304826
- Billiard Gray
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.
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RH975S 2024 Nightster™ Special
$13,949.00 $10,999.00- 305263
- Pre-owned
- 2024
- 8021 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1ZF114RB305263
- Billiard Gray
With modern function and traditional form, the Harley-Davidson® Nightster Special has a liquid-cooled V-twin engine and a classic Sportster® silhouette.
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RH975S 2024 Nightster™ Special
$13,799.00 $11,999.00- 308389
- Pre-owned
- 2024
- 449 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1ZF118RB308389
- Billiard Gray
With modern function and traditional form, the Harley-Davidson® Nightster Special has a liquid-cooled V-twin engine and a classic Sportster® silhouette.
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RH975S 2023 Nightster™ Special
$15,199.00 $10,999.00- 308530
- Pre-owned
- 2023
- 52 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1ZF119PB308530
- BRT BILIARD BLU
Harley-Davidson® introduces a new middle-weight contender that combines classic Sportster® silhouette with the sophisticated performance of the Revolution® Max 975T engine. Adding to the already successful mix of style, convenience and technology found in Nightster™, upgrades and new features on …