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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Harley-Davidson® Street Glide® Special 2021 FLHXS BLACK JACK METALLIC $28,499.00 $19,999.00

676679

Pre-owned

2021

15728 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KRP17MB676679

Black Jack Metallic

The custom hot rod bagger look stops people in their tracks. Now powered up with the Milwaukee-Eight® 114 engine, you’ll leave them in your dust.

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Harley-Davidson® Street Glide® 2021 FLHX BILLIARD RED $27,099.00 $16,499.00

602539

Pre-owned

2021

21622 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KBC1XMB602539

Billiard Red

The icon you love to see and love to be seen on. Powered by a Milwaukee-Eight® 107 engine, the Street Glide® lives up to its name with a fully adjustable rear suspension and a responsive front end that let you hum smoothly along rolling highways and winding roads. Its hot-rod bagger style and …

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Harley-Davidson® Road Glide® Special 2021 FLTRXS MIDNIGHT CRIMSON $29,099.00 $22,499.00

608168

Pre-owned

2021

21248 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KTP19MB608168

Midnight Crimson

Blacked-out and loaded with premium features. Fire up the thrill-inducing Milwaukee-Eight® 114 V-Twin engine and you’re in for one hell of a ride.

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Harley-Davidson® Pan America™ 1250 Special 2021 RA1250S GAUNTLET GRAY METALLIC $20,199.00 $10,999.00

315327

Pre-owned

2021

23113 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1ZES18MB315327

Gauntlet Gray Metallic

The Pan America™ 1250 Special motorcycle is our premier two-wheel multi-tool built to endure, designed to explore, and engineered for adventure.

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Harley-Davidson® Heritage Classic 107 2021 FLHC VIVID BLACK - BLACK FINISH $19,949.00 $14,999.00

033446

Pre-owned

2021

10641 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YAJ11MB033446

Vivid Black

The refined gloss-black finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. It starts with the performance of the Milwaukee-Eight® 107 or 114 engine and the re-invented Softail® frame and suspension. The ride will put a big smile on your face. …

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Harley-Davidson® Heritage Classic 107 2021 FLHC VIVID BLACK $18,999.00 $10,999.00

022444

Pre-owned

2021

41565 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YAJ18MB022444

Vivid Black

The refined gloss-black finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. It starts with the performance of the Milwaukee-Eight® 107 or 114 engine and the re-invented Softail® frame and suspension. The ride will put a big smile on your face. …

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FXST 2021 Softail Standard® $14,999.00 $9,999.00

059287

Pre-owned

2021

1065 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1BVJ14MB059287

Vivid Black

A stripped-down, souped-up, bobber with a post WWII era look. You get the power and soul-satisfying sound of the Milwaukee-Eight® 107 V-Twin to take you into the future. Fast.

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FXFBS 2021 Fat Bob® 114 $19,199.00 $14,499.00

059472

Pre-owned

2021

1155 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YLK18MB059472

Billiard Red

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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FLTRK 2021 Road Glide® Limited $29,799.00 $20,999.00

635406

Pre-owned

2021

12935 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KZF17MB635406

Midnight Crimson

A fully loaded Grand Touring machine with 114 cubic inches of power and new premium finishes. Enjoy the ride to the fullest.

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FLSB 2021 Sport Glide® $19,249.00 $13,999.00

063309

Pre-owned

2021

5617 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YMJ17MB063309

Stone Washed White Pearl

Devour endless miles of highway. Lean hard through twisting roads. Hit the night spots. Adventure is yours for the taking on the Sport Glide™.

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FLHX 2021 Street Glide® $22,499.00 $16,499.00

610388

Pre-owned

2021

12724 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KBC10MB610388

Vivid Black

The icon you love to see and love to be seen on. Powered by a Milwaukee-Eight® 107 engine, the Street Glide® lives up to its name with a fully adjustable rear suspension and a responsive front end that let you hum smoothly along rolling highways and winding roads. Its hot-rod bagger style and …

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FLHTKSE 2021 CVO™ Limited $35,999.00

B956103

Pre-owned

2021

8863 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1TEH11MB956103

Bronze Armor

The ultimate in Grand American Touring. Best-in-class Twin-Cooled™ Milwaukee-Eight® 117 power, show-stopping paint, Tomahawk™ wheels and premium comfort for you and your passenger. Is this too much motorcycle for everyone? No. That’s the whole point.

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