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Harley-Davidson® Heritage Softail® Classic 2015 FLSTC BLACK W/ PINSTRIPE
$19,499.00 $10,195.00- 021830
- Pre-owned
- 2015
- 25479 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1BWV13FB021830
- Vivid Black
The perfect marriage of styling that dates back 80-odd years, and technology that’s bang up to date. With its classy whitewalls, full fenders and leather-studded saddlebags, the Heritage gives you 40s styling in spades.This year we’ve improved the braking system to give it an even better feel with …
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Harley-Davidson® Heritage Softail® Classic 2008 FLSTC PAC BLUE/BLK W/PINSTRIPE
$18,600.00 $7,999.00- Y038218
- Pre-owned
- 2008
- 46000 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BW5188Y038218
- PAC BLUE/BLK W/PINSTRIPE
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Harley-Davidson® Heritage Softail® Classic 2008 FLSTC CRIMSON RED SUN W/PINSTRIPE
$18,599.00 $7,999.00- 065551
- Pre-owned
- 2008
- 62616 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BW51X8Y065551
- CRIMSON RED SUN W/PINSTRIPE
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Harley-Davidson® Heritage Softail® Classic 2007 FLSTC DEEP COBALT
$16,899.00 $8,999.00- 037175
- Pre-owned
- 2007
- 48011 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1BW5127Y037175
- DEEP COBALT
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Harley-Davidson® Heritage Softail® Classic 2005 FLSTC Luxury Blue
$15,669.00 $4,999.00- 014059
- Pre-owned
- 2005
- 66918 mi
- Harley-Davidson®
- Starved Rock Harley-Davidson
- 1HD1BWB145Y014059
- Luxury Blue
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Harley-Davidson® Heritage Softail® Classic 2004 FLSTCI GOLD/BLACK W/PINSTRIPE
$18,180.00 $7,499.00- 087118
- Pre-owned
- 2004
- 19646 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BWB194Y087118
- GOLD/BLACK W/PINSTRIPE
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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® 2026 FLHC DRK BILIARD GRY
Call for price- TB021740
- New
- 2026
- 3 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1YA913TB021740
- DRK BILIARD GRY
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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Harley-Davidson® Heritage Classic 2026 FLHC Midnight Ember w/Laced Wheels
Call for price- 024275
- New
- 2026
- 6 mi
- Harley-Davidson®
- Starved Rock Harley-Davidson
- 1HD1YA916TB024275
- Midnight Ember w/Laced Wheels
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Harley-Davidson® Heritage Classic 2025 FLHC WHISKEY FIRE/BLK
Call for price- SB017127B
- New
- 2025
- 14 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1YA912SB017127
- Whiskey Fire / Vivid Black w/Cast 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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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 2024 FLHCS ATLAS SLV MTLIC
Call for price- RB040299
- New
- 2024
- 20 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1YBK10RB040299
- Atlas Silver Metallic - Black Finish
A quintessential American cruiser, the Harley-Davidson® Heritage Classic 114 has showstopping vintage details and pure rock ‘n’ roll style.