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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 …
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FLHXST 2023 Street Glide® ST
$29,999.00$23,995.00- 628316
- Pre-owned
- 2023
- 3179 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1ABL10PB628316
- Vivid Black
Elevated pro-touring bagger performance and style for the rider who just can’t ever get enough. The Street Glide™ ST model pairs the muscular Milwaukee-Eight® 117 powertrain with tough West Coast styling influences and new dark-and-bronze finishes. Undiminished rider comfort and the iconic batwing …
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FLHXST 2022 Street Glide® ST
$24,999.00- 629394
- Pre-owned
- 2022
- 8425 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1ABL17NB629394
- Vivid Black
Elevated pro-touring bagger performance and style for the rider who just can’t ever get enough. The Street Glide™ ST model pairs the muscular Milwaukee-Eight® 117 powertrain with tough West Coast styling influences and new dark-and-bronze finishes. Undiminished rider comfort and the iconic batwing …
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FLHXST 2022 Street Glide® ST
$30,199.00$22,995.00- 645978
- Pre-owned
- 2022
- 14153 mi
- Harley-Davidson®
- Windy City Harley-Davidson®
- 1HD1ABL13NB645978
- Vivid Black
Elevated pro-touring bagger performance and style for the rider who just can’t ever get enough. The Street Glide™ ST model pairs the muscular Milwaukee-Eight® 117 powertrain with tough West Coast styling influences and new dark-and-bronze finishes. Undiminished rider comfort and the iconic batwing …
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FLHXSE 2026 CVO Street Glide
- TB955448
- New
- 2026
- 2 mi
- Harley-Davidson®
- Woodstock Harley-Davidson®
- 1HD1PX616TB955448
- Torched Orange CVO Tri-Tone
For riders who recognise the details, the 2026 Harley-Davidson® CVO™ Street Glide® sets the standard. Every line, every square inch of paint, and every single touchpoint on this bike is curated with obsession, from its Torched Orange paint and an amber-tinted windshield to exclusive Carbide …
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FLHXSE 2025 CVO™ Street Glide™
- 958720
- New
- 2025
- 2 mi
- Harley-Davidson®
- Illinois Harley-Davidson®
- 1HD1PX612SB958720
- Poison Berry
Equipped with the best of everything straight from the factory, the CVO Street Glide is a Batwing bagger loaded with the latest tech and premium custom detailing—like the VVT 121 engine, high-performance audio, exclusive paint, and contrast-cut wheels—setting the stage for unmatched performance and …