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UNKNOWN

V BLK/BLK ICE

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Whiskey Fire

WHITE

White Gold Pearl

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White Onyx Pearl

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WHITE ONYX PRL

White Sand Pearl

WHSKY/V BLK W/PINSTRIPE

WHT GOLD/COBALT W/PINSTRIPE

Wicked Red

WKDRED/TWTDCHRY

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Chicago Harley-Davidson®

Illinois Harley-Davidson®

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FLHC 2026 Heritage Classic®

Click for Price

TB032279

New

2026

5 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YA91XTB032279

Vivid Black Black Laced Wheels

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

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FLHC 2025 Heritage Classic

$24,999.00

$22,999.00

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026659

Pre-owned

2025

972 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YA913SB026659

Vivid Black w/Laced Wheels

Classic cruiser vibes meet hot rod swagger—the Heritage Classic lets you switch things up fast, giving you the versatility to roll out for a weekend trip or strip it down for a laid-back ride around town.

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FLHC 2021 Heritage Classic 107

$21,049.00

$13,999.00

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B049105

Pre-owned

2021

14674 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YAJ10MB049105

Deadwood Green/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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FLHC 2018 Heritage Classic

$19,949.00

$12,999.00

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073795

Pre-owned

2018

16423 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YAJ19JC073795

INDGRYDNM/BLKDM W/PINSTRIPE

The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

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FLHC 2018 Heritage Classic

$19,949.00

$13,999.00

Click for Price

029384

Pre-owned

2018

24807 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YAJ1XJC029384

Silver Fortune

The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

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FLFBS 2024 Fat Boy™ 114

$21,999.00

$17,999.00

Click for Price

017290

Pre-owned

2024

1703 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YGK13RB017290

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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FLFBS 2023 Fat Boy® 114

$21,699.00

$15,499.00

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030564

Pre-owned

2023

812 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YGK16PB030564

BRT BILIARD BLU

The original fat custom icon. Now lighter than the previous generation Fat Boy 114, and slinging torque from a Milwaukee-Eight® 114. You’ll feel the difference the instant you crack the throttle.

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FLFBS 2023 Fat Boy® 114

$20,399.00

$14,999.00

Click for Price

047003

Pre-owned

2023

15627 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YGK17PB047003

Bright Billiard Blue

The original fat custom icon. Now lighter than the previous generation Fat Boy 114, and slinging torque from a Milwaukee-Eight® 114. You’ll feel the difference the instant you crack the throttle.

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FLFBS 2020 Fat Boy® 114

$21,949.00

$16,999.00

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LB012674

Pre-owned

2020

7588 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YGK18LB012674

Stiletto Red

The name may be Fat Boy®, but the look is all muscle. This is the icon, riding on a 240mm rear tyre, 160mm front tyre and solid disc wheels. You get satin chrome finishes and signature LED lighting. This version is 14 kilograms lighter than the previous generation Fat Boy models, and its slinging …

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FLFBS 2019 Fat Boy® 114

$20,849.00

$14,999.00

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019987

Pre-owned

2019

14689 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YGK2XKB019987

Scorched Orange/Black Denim

The name may be Fat Boy®, but the look is all muscle. This is the icon, riding on a 240mm rear tyre, 160mm front tyre and solid disc wheels. You get satin chrome finishes and signature LED lighting. This version is 14 kilograms lighter than the previous generation Fat Boy models, and its slinging …

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FLFB 2025 Fat Boy®

$23,249.00

$21,999.00

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039908

Pre-owned

2025

218 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YF911SB039908

Vivid Black

Adored since day one, the singular Fat Boy stands out with bright chrome and bold finishes, and now it is better than ever with a big Milwaukee-Eight® 117 Custom V-twin engine.

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FLDE 2020 Deluxe

$19,459.00

$15,999.00

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025617

Pre-owned

2020

1271 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YCJ13LB025617

Vivid Black

The look of the Softail® Deluxe has always been deluxe. It’s the classic showstopper — born to stand out on a run down the Vegas strip. Now, underneath the bright chrome, you’ve got the ride of a seriously modern machine. Thirty-one pounds lighter, easier handling, massive power and acceleration, …

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