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Harley-Davidson® Heritage Softail® Classic 2002 FLSTCI RICH RED W/STRIPES
$16,800.00 $4,999.00- 089045
- Pre-owned
- 2002
- 72138 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1BWB102Y089045
- RICH RED W/STRIPES
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Harley-Davidson® Heritage Classic 114 2024 FLHCS VIVID BLACK W/ PINSTRIPE
$19,999.00- RB035289
- Pre-owned
- 2024
- 27233 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1YBK15RB035289
- Vivid Black - Black Finish
A quintessential American cruiser, the Harley-Davidson® Heritage Classic 114 has showstopping vintage details and pure rock ‘n’ roll style.
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Harley-Davidson® Heritage Classic 114 2022 FLHCS REDLINE RED/BLK W/PS
$19,799.00 $13,999.00- 013555
- Pre-owned
- 2022
- 18127 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1YBK18NB013555
- Redline Red/Vivid Black (Black Finish w/Cast Wheels)
The dark style, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place.
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Harley-Davidson® Heritage Classic 107 2021 FLHC VIVID BLACK - BLACK FINISH
$19,949.00 $14,999.00- 033446
- Pre-owned
- 2021
- 10641 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1YAJ11MB033446
- Vivid Black
The refined gloss-black finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. It starts with the performance of the Milwaukee-Eight® 107 or 114 engine and the re-invented Softail® frame and suspension. The ride will put a big smile on your face. …
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Harley-Davidson® Heritage Classic 107 2021 FLHC VIVID BLACK
$18,999.00 $10,999.00- 022444
- Pre-owned
- 2021
- 41565 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1YAJ18MB022444
- Vivid Black
The refined gloss-black finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. It starts with the performance of the Milwaukee-Eight® 107 or 114 engine and the re-invented Softail® frame and suspension. The ride will put a big smile on your face. …
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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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Harley-Davidson® Freewheeler™ 2015 FLRT SUPERIOR BLUE
$25,699.00 $16,999.00- 860454
- Pre-owned
- 2015
- 19937 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1MCM17FB860454
- Superior Blue
Harley-Davidson puts hot-rod swagger on three wheels with the 2015 Freewheeler™ motorcycle, the all-new trike model that fuses pure custom style and easy-handling performance. From its ape-hanger handlebar to its bobtail fenders the Freewheeler is a page ripped straight from the bad- attitude …
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Harley-Davidson® Fat Boy™ 114 2024 FLFBS SHARKSKIN
$21,499.00 $17,499.00- 019556
- Pre-owned
- 2024
- 1341 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1YGK13RB019556
- Sharkskin Blue
The original fat custom icon. Loved since day one, the Harley-Davidson® Fat Boy 114 stands out with bright chrome and bold finishes.
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Harley-Davidson® Fat Boy™ 114 2024 FLFBS RED ROCK
$21,999.00 $18,999.00- 040404
- Pre-owned
- 2024
- 459 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1YGK18RB040404
- Red Rock
The original fat custom icon. Loved since day one, the Harley-Davidson® Fat Boy 114 stands out with bright chrome and bold finishes.
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Harley-Davidson® Fat Bob® 114 2022 FXFBS WHITE SAND PRL
$20,999.00 $12,999.00- 014677
- Pre-owned
- 2022
- 4876 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1YLK18NB014677
- White Sand Pearl
The Fat Bob® is all Harley-Davidson, but at the same time, it’s unlike any Harley® motorcycle that ever existed before. From the modern, aggressive look of its 2-1-2 upswept exhaust and tarmac-devouring fat tyres to the massive torque of the Milwaukee-Eight® engine to the ride of the Softail® frame,…
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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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Harley-Davidson® Fat Bob® 107 2019 FXFB BLACK
$10,999.00MSRP: $17,049.00 - 029281
- Pre-owned
- 2019
- 56492 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1YKJ23KB029281
- Black Denim
The Fat Bob® is all Harley-Davidson, but at the same time, it’s unlike any Harley® motorcycle that ever existed before. From the modern, aggressive look of its 2-1-2 upswept exhaust and tarmac-devouring fat tyres to the massive torque of the Milwaukee-Eight® engine to the ride of the Softail® frame,…