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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FLSTC 2014 Heritage Softail® Classic $19,479.00 $10,999.00

EB036949

Pre-owned

2014

9626 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1BWV16EB036949

BIG BLUE/V BLK W/ PINSTRIPE

The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …

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FLHXS 2014 Street Glide® Special $22,499.00 $12,999.00

677780

Pre-owned

2014

18995 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KRM14EB677780

BLACK W/ PINSTRIPE

Enhanced by Project RUSHMORE, the new- for-2014 Street Glide® Special takes the hot-rod bagger formula a little further, adding a Gloss Black inner fairing, Reflex™ Linked Brakes with ABS, the Boom!™ Box 6.5 GT infotainment system and CVO™-style hand-adjustable lowered rear suspension as standard …

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FLHXS 2014 Street Glide® Special $22,499.00 $13,999.00

691225

Pre-owned

2014

8070 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KRM12EB691225

MYSTERIOUS RED W/ PINSTRIPE

Enhanced by Project RUSHMORE, the new- for-2014 Street Glide® Special takes the hot-rod bagger formula a little further, adding a Gloss Black inner fairing, Reflex™ Linked Brakes with ABS, the Boom!™ Box 6.5 GT infotainment system and CVO™-style hand-adjustable lowered rear suspension as standard …

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FLHXS 2014 Street Glide® Special $23,209.00 $17,999.00

668090

Pre-owned

2014

17457 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KRM10EB668090

BLACKND CAYENNE W/ PINSTRIP

Enhanced by Project RUSHMORE, the new- for-2014 Street Glide® Special takes the hot-rod bagger formula a little further, adding a Gloss Black inner fairing, Reflex™ Linked Brakes with ABS, the Boom!™ Box 6.5 GT infotainment system and CVO™-style hand-adjustable lowered rear suspension as standard …

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FLHTK 2014 Electra Glide® Ultra Limited $25,899.00 $12,995.00

665291

Pre-owned

2014

11063 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KEL13EB665291

MYS RED/CAYENNE W/ PINSTRIP

The 2014 Ultra Limited® is a premium touring bike full of authentic Harley-Davidson® grand American touring style. As part of Project RUSHMORE, it has been redesigned for 2014 and features a new twin-cooled high output Twin Cam 103™ engine with more low-end torque and passing power and is combined …

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FLHTCUTG 2014 Tri Glide® Ultra $34,499.00 $23,999.00

852318

Pre-owned

2014

39556 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1MAL18EB852318

MYS RED/CAYENNE W/ PINSTRIP

The new for 2014 Tri Glide® Ultra Classic® provides long-haul, 3-wheel touring comfort and confidence. As part of Project RUSHMORE, it features the new twin-cooled high output Twin Cam 103™ engine, built to deliver more power for passing, climbing hills and carrying a passenger and luggage. This is …

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FLHTCUTG 2014 Tri Glide® Ultra $34,499.00 $23,999.00

858314

Pre-owned

2014

12977 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1MAL18EB858314

MYS RED/CAYENNE W/ PINSTRIP

The new for 2014 Tri Glide® Ultra Classic® provides long-haul, 3-wheel touring comfort and confidence. As part of Project RUSHMORE, it features the new twin-cooled high output Twin Cam 103™ engine, built to deliver more power for passing, climbing hills and carrying a passenger and luggage. This is …

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FLHR 2014 Road King® $19,054.00 $12,995.00

666521

Pre-owned

2014

36371 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1FBM18EB666521

BIG BLUE/V BLK W/ PINSTRIPE

The 2014 Road King® Classic takes the idea of Classic to the most modern place it's ever been. As part of Project RUSHMORE, it has been redesigned for 2014 to make the ride better than it's ever been. The bike is powered with a new rubber-mounted high output Twin Cam 103™ engine that gives you more …

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FLD 2014 Switchback™ $15,849.00 $8,499.00

322252

Pre-owned

2014

40284 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1GZM18EC322252

BLACK

The 2014 Switchback with detachable saddlebags and windshield is perfect for both cruising and touring. Powered by a Twin Cam 103™ engine with smooth shifting Six-Speed Cruise Drive transmission and with a light-weight chassis and cast aluminium wheels, the Switchback offers easy-handling. Its 2-…

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2014 Harley-Davidson® Softail Slim® Vivid Black $17,999.00 $11,999.00

050941

Pre-owned

2014

24373 mi

Harley-Davidson®

Starved Rock Harley-Davidson

1HD1JRV1XEB050941

Vivid Black

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Harley-Davidson® Ultra Classic® Electra Glide® 2013 FLHTCU EMBR RED SUNGLO W/ PINSTRIP $23,039.00 $10,999.00

669566

Pre-owned

2013

43708 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1FCM16DB669566

EMBR RED SUNGLO W/ PINSTRIP

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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Harley-Davidson® Street Glide® 2013 FLHX CHRM YELLOW PRL $19,799.00 $13,999.00

663569

Pre-owned

2013

23912 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1KBM17DB663569

CHRM YELLOW PRL

The Street Glide® is a bagger with street-wise soul, such as stripped down trim and chrome, low suspension, and blackened, cropped wind deflector. Inspired by the street, the Street Glide is ready to roar with attitude. The innovative Harley-Davidson® Touring chassis is based on a single-spar, …

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