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®

Illinois Harley-Davidson®

Starved Rock Harley-Davidson

Windy City Harley-Davidson®

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FLHTCU 2011 Electra Glide® Ultra Classic® $22,199.00 $9,499.00

662300

Pre-owned

2011

37010 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1FC413BB662300

UNKNOWN

The Ultra Classic® Electra Glide® sets the standard for long-haul touring comfort and convenience. Though many imitators sought to duplicate it, the Ultra Classic Electra Glide stands tall as a benchmark for touring enthusiasts. A fourspeaker, 80-watt Harmon/Kardon® Advanced Audio System, one-piece,…

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FLHTCU 2011 Electra Glide® Ultra Classic® $22,399.00 $11,999.00

658116

Pre-owned

2011

21000 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1FC411BB658116

MERLOT/BLK

The Ultra Classic® Electra Glide® sets the standard for long-haul touring comfort and convenience. Though many imitators sought to duplicate it, the Ultra Classic Electra Glide stands tall as a benchmark for touring enthusiasts. A fourspeaker, 80-watt Harmon/Kardon® Advanced Audio System, one-piece,…

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FLHTC 2011 Electra Glide® Classic $5,500.00

655598

Pre-owned

2011

50698 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1FF416BB655598

SILVER

With features like a spacious Tour-Pak® carrier, a Harmon/Kardon® Advanced Audio System and fine Harley-Davidson styling detail, the Electra Glide® Classic model brings a level of luxury to touring adventures. The innovative Harley-Davidson® Touring chassis is based on a single-spar, rigid backbone …

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FLHR 2011 Road King® $18,999.00 $11,499.00

665682

Pre-owned

2011

27940 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1FB410BB665682

COOL BLUE/V BLK

When the original Harley-Davidson® Road King® motorcycle was introduced in 1994, it didn't take long for it to obtain iconic status with heritage going back to the original 1965 Electra Glide® model. It may look like a timeless boulevard cruiser, but it is also a fully equipped, long-distance …

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2011 Harley-Davidson® Super Glide® Custom Vivid Black $14,999.00 $8,999.00

322170

Pre-owned

2011

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1GV410BC322170

Vivid Black

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2011 Harley-Davidson® Electra Glide® Ultra Classic® Vivid Black $20,969.00 $9,499.00

654705

Pre-owned

2011

56825 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1FC410BB654705

Vivid Black

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2011 Softail® Deluxe $17,864.00 $10,999.00

031915

Pre-owned

2011

11383 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1JD514BB031915

BLACK W/PINSTRIPE

One of the most confidence-inspiring Big Twins, the Softail® Deluxe features an extremely low seat with "collapsing sides," pull back handlebar and riser, and easy-reach, extended kickstand. The powerful, counter-balanced Twin Cam 96B™ and 6-Speed Cruise Drive® transmission are appreciated by many …

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XL 883N 2010 Iron 883™ $7,999.00 $5,999.00

419524

Pre-owned

2010

15203 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD4LE219AC419524

BLACK DENIM

The Iron 883™ pushes minimal Dark Custom styling to the edge with a V-Twin beat and gritty, old-school garage features. The $7,999 MSRP makes this model a great starting point for customization.Born on the gritty dirt tracks and drag strips of the 1950s, the Harley-Davidson® Sportster® represents …

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Harley-Davidson® Electra Glide® Ultra Classic® 2010 FLHTCU V BLK/BRIL SLVR $22,399.00 $6,999.00

602753

Pre-owned

2010

53739 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1FC416AB602753

V BLK/BRIL SLVR

The Ultra Classic® Electra Glide® provides long-haul touring comfort, convenience, and cargo capacity, with unmistakable Harley style.The innovative Harley-Davidson® Touring chassis is based on a single-spar, rigid backbone frame and a stout swingarm developed to withstand the demands of long-haul …

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Harley-Davidson® Electra Glide® Ultra Classic® 2010 FLHTCU FLM BLUE/SILVER $22,399.00 $10,999.00

651956

Pre-owned

2010

40935 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1FC411AB651956

FLM BLUE/SILVER

The Ultra Classic® Electra Glide® provides long-haul touring comfort, convenience, and cargo capacity, with unmistakable Harley style.The innovative Harley-Davidson® Touring chassis is based on a single-spar, rigid backbone frame and a stout swingarm developed to withstand the demands of long-haul …

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FXDFSE2 2010 CVO™ Fat Bob® $14,999.00 $8,999.00

300369

Pre-owned

2010

3883 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1GY411AC300369

BLACK

The Harley-Davidson® CVO™ Fat Bob® is a limited-production custom motorcycle that projects an agressive, super-duty presence behind a beefy front wheel, twisted Tommy Gun exhaust, bold paint and innovative custom styling.The CVO Fat Bob is based on the Harley-Davidson Dyna platform, which pairs Big …

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FLHX 2010 Street Glide® $18,999.00 $9,999.00

659622

Pre-owned

2010

50158 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KB414AB659622

BLACK

The redesigned Street Glide® is a bagger with hot-rod soul, with minimal trim and chrome, lowered suspension, and black slotted aluminum wheels. Inspired by the street, but still ready for the long road.The innovative Harley-Davidson® Touring chassis is based on a single-spar, rigid backbone frame …

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