NEW HARLEY-DAVIDSON® MOTORCYCLE INVENTORY

Explore new 2025 & 2026 Harley-Davidson® models for sale at Windy City Harley-Davidson® in Libertyville, IL

Find your next new motorcycle when you work with the experts at Windy City Harley-Davidson^®! We offer a huge selection of hundreds of new bikes for sale, so we're sure to have something in stock to fit your riding needs!

Why Buy From Us?

Anyone can sell you a motorcycle. What sets us apart is what happens after. We believe in treating people like family, not numbers, and making sure every rider feels supported long after they leave the showroom. From service and parts to events and community, we’re here for the long haul — because your experience shouldn’t end when the sale does.

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UNKNOWN

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Chicago Harley-Davidson®

Illinois Harley-Davidson®

Starved Rock Harley-Davidson

Windy City Harley-Davidson®

Woodstock Harley-Davidson®

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FXFBS 2019 Fat Bob® 114 $19,249.00 $12,999.00

KC018974

Pre-owned

2019

6297 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YLK14KC018974

Scorched Orange/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,…

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FXBB 2019 Street Bob® $14,549.00 $11,495.00

066746

Pre-owned

2019

2458 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YJJ25KB066746

Vivid Black

The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

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FLTRXS 2019 Road Glide® Special $29,589.00 $21,499.00

623939

Pre-owned

2019

5757 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KTP13KB623939

UNKNOWN

The Road Glide® Special model gets a blacked-out Milwaukee-Eight® 114 (1868cc) engine standard this year. Which means our darkest, most road-devouring road machine goes to an even darker, more road-hungry place. You get the all-new big screen BOOM! ™ GTS infotainment system, premium Talon wheels, …

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FLTRX 2019 Road Glide® $21,589.00 $16,999.00

668087

Pre-owned

2019

6359 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KHC11KB668087

Vivid Black

The menacing dual Daymaker™ Reflector LED headlamps in the Road Glide® motorcycle’s shark-nose fairing are a familiar sight on the highway. It’s the machine of choice for hard-charging riders. You get Milwaukee-Eight® 107 (1745cc) power, easily adjustable emulsion rear suspesion and responsive …

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FLTRU 2019 Road Glide® Ultra $30,089.00 $22,999.00

628704

Pre-owned

2019

28000 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KGF10KB628704

Twisted Cherry

The Road Glide® Ultra is the choice of the highest-mileage riders in the Harley-Davidson family. For good reason. You get a frame-mounted shark-nose fairing, 13.5-inch windscreen and dual Daymaker™ Reflector LED headlamp. And the power of a Twin-Cooled™ Milwaukee-Eight® 114 (1868cc) V-Twin engine. …

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FLSL 2019 Softail Slim® $16,349.00 $13,499.00

063477

Pre-owned

2019

5223 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YDJ29KB063477

Bonneville Salt Denim

The stripped-down, souped-up, post WWII era look of the bobber is running stronger than ever in the Softail Slim® model. You get the classic look of spoked wheels, chopped mudguards and footboards. And a ride straight out of right now. It’s 16 kilograms lighter, with greater lean angle, than Slim …

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FLHXSE 2019 CVO™ Street Glide® $41,089.00 $28,999.00

951897

Pre-owned

2019

4757 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1PXL10KB951897

Black Forest

There’s the best, and there’s all the rest. When it comes to custom touring, the CVO™ Street Glide® model is as far up the ladder as you can go. You get the power of the Milwaukee-Eight® 117 (1923cc) V-Twin engine, red rocker covers, premium Talon wheels and custom controls, all-new BOOM!™ Box GTS …

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FLHXS 2019 Street Glide® Special $27,589.00 $20,499.00

617894

Pre-owned

2019

23384 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRP16KB617894

Vivid Black

The Street Glide® Special model kicks the hot rod bagger style into a higher gear. It starts with the Milwaukee-Eight® 114 (1868cc) engine that comes standard this year. When you twist the throttle, hold on tight. You also get the all-new, big screen BOOM! ™ GTS infotainment system. Then there’s …

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FLHX 2019 Street Glide® $21,289.00 $16,499.00

629118

Pre-owned

2019

4546 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KBC14KB629118

Kinetic Green

The mould for the factory hot rod bagger was cut the day the Street Glide® motorcycle rolled off the line. It’s spawned imitators, but none measure up. The look is backed up by the refined power of a Milwaukee-Eight® 107 (1747cc) engine. It combines with a fully adjustable rear suspension, …

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FLHTK 2019 Ultra Limited $29,139.00 $17,999.00

613088

Pre-owned

2019

36003 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KEF10KB613088

UNKNOWN

From its new Twin-Cooled™ Milwaukee-Eight® 114 (1868cc) V-Twin engine right down to its heated hand grips, the Ultra Limited has it all. Batwing fairing and splitstream air vent for optimal air flow and reduced head buffeting. All new BOOM!™ GTS infotainment system. Electronic cruise control, …

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FLFBS 2019 Fat Boy® 114 $20,849.00 $14,999.00

019987

Pre-owned

2019

14689 mi

Harley-Davidson®

Woodstock 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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2019 Harley-Davidson® Ultra Limited Vivid Black $26,799.00 $20,499.00

659367

Pre-owned

2019

14412 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1KEF13KB659367

Vivid Black

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