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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Showing 157 - 168 of 221 results

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FLHX 2026 Street Glide®

TB627653

New

2026

10 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KB710TB627653

DRK BILIARD GRY

For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

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FLHX 2026 Street Glide®

TB625103

New

2026

2 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1KB71XTB625103

DRK BILIARD GRY

For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

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FLHX 2026 Street Glide®

TB621315

New

2026

5 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1KB715TB621315

DRK BILIARD GRY

For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

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FLHX 2026 Street Glide®

TB618549

New

2026

5 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1KB714TB618549

DRK BILIARD GRY

For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

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FLHLTSE 2026 CVO Street Glide 3 Limited

TB956257

New

2026

10 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1TN614TB956257

Citrus Heat CVO Tri-Tone

Trust us when we say this is a whole different kind of Trike. At the heart of the CVO Street Glide 3 Limited is the Milwaukee-Eight® VVT 121 motor, paired with a redesigned suspension and a new electric reverse system that make three-wheel touring feel commanding and assured. Heated seats, a trunk, …

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FLHLT 2026 Street Glide 3 Limited

TB857873

New

2026

2 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1MGN1XTB857873

Purple Abyss / Vivid Black Chrome Trim

The new 2026 Street Glide 3 Limited doesn’t echo the past. Instead, it creates its own language of long-haul touring. With the newly redesigned Batwing fairing, completely re-engineered suspension, and Milwaukee-Eight® VVT 117 power, every mile feels sharper, more comfortable, and more your own. …

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FLHLT 2026 Street Glide 3 Limited

TB855987

New

2026

2 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1MGN14TB855987

OLIV STL MTL/BLK W/ PINSTRI

The new 2026 Street Glide 3 Limited doesn’t echo the past. Instead, it creates its own language of long-haul touring. With the newly redesigned Batwing fairing, completely re-engineered suspension, and Milwaukee-Eight® VVT 117 power, every mile feels sharper, more comfortable, and more your own. …

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FLHC 2026 Heritage Classic®

TB036279

New

2026

2 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YA918TB036279

Brilliant Red Black Laced Wheels

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

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FLHC 2026 Heritage Classic®

TB036199

New

2026

2 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YA91XTB036199

Midnight Ember w/Laced Wheels

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

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FLHC 2026 Heritage Classic®

TB036794

New

2026

10 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YA912TB036794

Midnight Ember w/Laced Wheels

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

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FLHC 2026 Heritage Classic®

TB035389

New

2026

6 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YA91XTB035389

Teal Thunder / Vivid Black Black Cast Wheels

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

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FLHC 2026 Heritage Classic®

TB035250

New

2026

1 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1YA911TB035250

DRK BILIARD GRY

The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …

Find out more CHECK AVAILABILITY