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®

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Harley-Davidson® Street Glide® 2018 FLHX BLACK $21,699.00 $16,999.00

624219

Pre-owned

2018

19653 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KBC19JB624219

Vivid Black

There’s a pride that comes from riding the original, and when it comes to the stripped-down hot-rod look, that would be the Harley-Davidson® Street Glide® motorcycle. Its style is often copied but has never been equaled. The Milwaukee-Eight® 107 engine backs up the look with massive torque. The …

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Harley-Davidson® Road Glide® Ultra 2018 FLTRU SILVER/BLACK $27,699.00 $16,999.00

JB674857

Pre-owned

2018

41146 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KGD10JB674857

Silver Fortune/Black Tempest

Times have never been better for the riders who put on the most miles. Get behind the frame-mounted shark-nose fairing, 13.5-inch windscreen and dual Daymaker™ Reflector LED headlamps on the Road Glide® Ultra model, and you’ll know why. You’ve got a Twin-Cooled™ Milwaukee-Eight® 107 (1750cc) engine,…

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Harley-Davidson® Road Glide® 2018 FLTRX HC SHATTEREDFLK $22,489.00 $17,999.00

634900

Pre-owned

2018

6757 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1KHC17JB634900

HC SHATTEREDFLK

Those who appreciate the aggressive look and wind-cutting power of the frame-mounted shark- nose fairing and dual Daymaker™ Reflector LED headlamps on the Road Glide® motorcycle wouldn’t ride anything else. You’ve got the mountain-conquering power of the Milwaukee-Eight® 107 engine at the command …

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Harley-Davidson® Iron 883™ 2018 XL 883N BNVL SALT DENIM $9,549.00 $8,495.00

421090

Pre-owned

2018

2011 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD4LE211JC421090

Bonneville Salt Denim

Feel the purity of two wheels, a handle bar and an engine. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, the Iron 883™ model has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with …

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Harley-Davidson® Fat Bob® 114 2018 FXFBS INDSTRL GRY DNM $19,299.00 $11,499.00

034612

Pre-owned

2018

3993 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YLK18JC034612

INDSTRL GRY DNM

You can take the aggressive, futuristic look and adrenaline-pumping ride of the Fat Bob® as far as you want to go with Harley-Davidson® Genuine Motor Accessories and the Screamin’ Eagle® Milwaukee-Eight® 114 engine with Stage I upgrade.

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FXLR 2018 Low Rider® $18,995.00 $10,995.00

070492

Pre-owned

2018

9000 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YNJ1XJC070492

Wicked Red

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

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FXLR 2018 Low Rider® $15,399.00 $10,499.00

081069

Pre-owned

2018

18260 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YNJ1XJC081069

Vivid Black

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

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FXFBS 2018 Fat Bob® 114 $18,699.00 $11,495.00

034785

Pre-owned

2018

10339 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YLK16JC034785

INDSTRL GRYDNM

You can take the aggressive, futuristic look and adrenaline-pumping ride of the Fat Bob® as far as you want to go with Harley-Davidson® Genuine Motor Accessories and the Screamin’ Eagle® Milwaukee-Eight® 114 engine with Stage I upgrade.

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FXFBS 2018 Fat Bob® 114 $16,699.00 $11,999.00

038459

Pre-owned

2018

10641 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YLK12JC038459

Bonneville Salt Denim

You can take the aggressive, futuristic look and adrenaline-pumping ride of the Fat Bob® as far as you want to go with Harley-Davidson® Genuine Motor Accessories and the Screamin’ Eagle® Milwaukee-Eight® 114 engine with Stage I upgrade.

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FXFB 2018 Fat Bob® $16,999.00 $11,995.00

030296

Pre-owned

2018

10493 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YKJ1XJC030296

Black Denim

Something this groundbreaking can only come from Harley-Davidson. The all-new Fat Bob®. Twenty-two pounds lighter, massive Milwaukee-Eight® engine power, asphalt-eating traction, a pothole-devouring suspension, agile cornering, and a take-no-prisoners look. You get a 2-1-2 upswept exhaust, a never-…

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FLTRXS 2018 Road Glide® Special $26,299.00 $19,999.00

608464

Pre-owned

2018

6763 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KTC10JB608464

Vivid Black

This one’s for those who want to cut a wider swath. The aggressive looks and ride of the Road Glide® Special motorcycle take our most road-devouring machine to an even darker place. Note the blacked-out finishes on handlebars, . Right in the middle sits the thrill-inducing torque of the blacked-out …

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FLTRU 2018 Road Glide® Ultra $27,699.00 $20,999.00

650882

Pre-owned

2018

10744 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KGD10JB650882

Electric Blue

Times have never been better for the riders who put on the most miles. Get behind the frame-mounted shark-nose fairing, 13.5-inch windscreen and dual Daymaker™ Reflector LED headlamps on the Road Glide® Ultra model, and you’ll know why. You’ve got a Twin-Cooled™ Milwaukee-Eight® 107 (1750cc) engine,…

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