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FLSTC 2014 Heritage Softail® Classic
$19,479.00$10,999.00- 019745
- Pre-owned
- 2014
- 33927 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BWV14EB019745
- BIG BLUE/V BLK W/ PINSTRIPE
The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …
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FLSTC 2014 Heritage Softail® Classic
$19,479.00$10,999.00- EB036949
- Pre-owned
- 2014
- 9626 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BWV16EB036949
- BIG BLUE/V BLK W/ PINSTRIPE
The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …
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FLSTC 2009 Heritage Softail® Classic
$18,854.00$9,499.00- Y052293
- Pre-owned
- 2009
- 32824 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1BW5129Y052293
- BLACK W/PINSTRIPE
Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight …
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FLSTC 2004 Heritage Softail® Classic
$16,995.00$5,499.00- 073243
- Pre-owned
- 2004
- 16057 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1BJY154Y073243
- BLACK W/PINSTRIPE
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FLSTC 2002 Heritage Softail® Classic
$16,555.00$5,999.00- 044710
- Pre-owned
- 2002
- 32694 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1BJY112Y044710
- JADE SUNGLO W/STRIPES
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FLSB 2018 Sport Glide™
$18,999.00$10,999.00- 057762
- Pre-owned
- 2018
- 25026 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1YMJ2XJC057762
- UNKNOWN
Devour endless miles with some room for gear. Or strip it down and carve city streets. The all-new Sport Glide™ is locked and loaded for whatever, whenever. You’ll be riding on the most advanced frame we’ve ever offered — the completely redesigned Softail® Inverted front forks and a fully …
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FLS 2018 Softail Slim®
$16,299.00$11,999.00- 069597
- Pre-owned
- 2018
- 14728 mi
- Harley-Davidson®
- Chicago Harley-Davidson®
- 1HD1YDJ15JC069597
- BLUE
The idea behind bobbers has always been to strip down and soup up the bike for a more exciting ride. The all-new Softail Slim® takes that idea to the edge. It’s 35 pounds lighter than last year’s model. It’s got more power, more lean angle, and a redesigned front and rear suspension. So you can put …
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FLS 2015 Softail Slim®
$17,049.00$10,999.00- 032030
- Pre-owned
- 2015
- 19919 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1JRV19FB032030
- Two-Tone Amber Whiskey/Vivid Black
You may know the background? Back in the 40s servicemen returning after the war took old military Harleys® and stripped them back. They made several refinements, including chucking away the front fenders and ‘bobbing’ the rear ones. Hence the ‘Bobber’ was born. And here we are, still are more than …
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FLRT 2024 Freewheeler™
$32,199.00$26,499.00- 854643
- Pre-owned
- 2024
- 2934 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1MCP12RB854643
- Alpine Green / Vivid Black
The Harley-Davidson® Freewheeler delivers aggressive styling, enticing performance, and confident handling on three wheels.
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FLHXU 2000 Street Glide™ Ultra
- SB609522
- New
- 2025
- 13717 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1AK713SB609522
The Street Glide Ultra is made for two-up touring, with a powerful V-twin engine, spacious storage, and modern amenities refined over decades of cross-country riding.
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FLHXSTSE 2026 CVO Street Glide ST
- TB956694
- New
- 2026
- 2 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1TR819TB956694
- Inferno Gray
Introducing a new chapter in the CVO story: the 2026 CVO Street Glide ST. All new for 2026, the CVO Street Glide ST takes the Batwing bagger into uncharted territory. Its Heavy Breather intake gives it lungs to match its attitude, while floating front rotors, eight selectable ride modes (including …
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FLHXSTSE 2026 CVO Street Glide ST
- TB955381-1
- New
- 2026
- 2 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1TR815TB955381
- Inferno Gray
Introducing a new chapter in the CVO story: the 2026 CVO Street Glide ST. All new for 2026, the CVO Street Glide ST takes the Batwing bagger into uncharted territory. Its Heavy Breather intake gives it lungs to match its attitude, while floating front rotors, eight selectable ride modes (including …