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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Chicago Harley-Davidson®

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Windy City Harley-Davidson®

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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

B629118

Pre-owned

2019

4552 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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FLHT 2019 Electra Glide® Standard

660725

Pre-owned

2019

14755 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1FVC26KB660725

Vivid Black

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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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2019 Harley-Davidson® CVO™ Road Glide® Red Pepper & Magnetic Gray with Black Hole $42,999.00 $27,430.00

952416

Pre-owned

2019

60280 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1TCL11KB952416

Red Pepper & Magnetic Gray with Black Hole

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XL 1200NS 2018 Iron 1200™ $11,999.00 $6,499.00

420379

Pre-owned

2018

Harley-Davidson®

Chicago Harley-Davidson®

1HD1LP321JC420379

Vivid Black

If you’re looking for a clue on what the new Iron 1200™ is all about, look no further than the name. It all starts with the 1200cc Evolution® engine that gives you loads of famous Sportster® torque. It’s got a throwback look that goes right to the roots of Sportster, thanks to 70’s-inspired tank …

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Harley-Davidson® Ultra Limited 2018 FLHTK GRAY/BLACK DENIM $14,499.00

664923

Pre-owned

2018

19696 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KED18JB664923

Industrial Gray Denim/Black Denim

If you’re the kind who wants it all, the Ultra Limited model gives it to you. From the powerful Twin-Cooled™ Milwaukee-Eight®107 engine right down to the heated hand grips. The unmistakable Batwing fairing and splitstream air vent mean optimal air flow and reduced head buffeting. Premium BOOM!™ Box …

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Harley-Davidson® Ultra Limited 2018 FLHTK BLU/BLK $28,199.00 $16,499.00

617522

Pre-owned

2018

33711 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KWD10JB617522

BLU/BLK

If you’re the kind who wants it all, the Ultra Limited model gives it to you. From the powerful Twin-Cooled™ Milwaukee-Eight®107 engine right down to the heated hand grips. The unmistakable Batwing fairing and splitstream air vent mean optimal air flow and reduced head buffeting. Premium BOOM!™ Box …

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Harley-Davidson® Street Glide® Special 2018 FLHXS LEGEND BLUE DNM $26,699.00 $16,999.00

625936

Pre-owned

2018

52063 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KYC15JB625936

Legend Blue Denim

When it comes to hot rod baggers, the Street Glide® Special is way out front. You get the tire-smoking power of its blacked-out Milwaukee-Eight® 107 engine sitting at the heart of dark finishes that stretch from headlight to exhaust. A new 19-inch Talon front wheel and 18-inch rear wheel. Stretched …

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