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®

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Windy City Harley-Davidson®

Woodstock Harley-Davidson®

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Off-Road

FXST 2020 Softail Standard® $13,799.00 $12,999.00

056239

Pre-owned

2020

3800 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1BVJ12LB056239

Vivid Black

The new Softail® Standard motorcycle offers the essential Harley-Davidson® cruiser experience - a lean Bobber profile steeped in attitude, classic Vivid Black paint highlighted with gleaming chrome wheels and polished finishes, the dynamic performance of the Harley-Davidson® Softail® chassis and …

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FXST 2020 Softail Standard® $13,799.00 $12,999.00

053232

Pre-owned

2020

1121 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1BVJ16LB053232

Vivid Black

The new Softail® Standard motorcycle offers the essential Harley-Davidson® cruiser experience - a lean Bobber profile steeped in attitude, classic Vivid Black paint highlighted with gleaming chrome wheels and polished finishes, the dynamic performance of the Harley-Davidson® Softail® chassis and …

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FXLR 2020 Low Rider® $15,299.00 $12,499.00

028260

Pre-owned

2020

8173 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YNJ19LB028260

Billiard Red

The Low Rider® was inspired by the tradition of individualism that came roaring to life in the custom chopper era. The rake on its front end, dual gauges on the tank and ‘70s-inspired graphics leave no doubt about that. Only it’s built for rolling faster, harder and longer than any Low Rider® …

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FXBB 2020 Street Bob® $16,144.00 $12,999.00

075281

Pre-owned

2020

19702 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1YJJ19LB075281

River Rock Gray

The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

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FXBB 2020 Street Bob® $14,599.00 $12,999.00

066784

Pre-owned

2020

3983 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1YJJ11LB066784

BRACUDA SLV DNM W/PINSTRIPE

The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

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FXBB 2020 Street Bob® $15,549.00 $12,999.00

LB031329

Pre-owned

2020

14923 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1YJJ10LB031329

BRACUDA SLV DNM W/PINSTRIPE

The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

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FLTRK 2020 Road Glide® Limited $29,599.00 $20,999.00

608125

Pre-owned

2020

31800 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KZF19LB608125

BRSLVDNM/BLKDNM W/PINSTRIPE

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FLTRK 2020 Road Glide® Limited $28,299.00 $19,999.00

636412

Pre-owned

2020

25694 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1KZF19LB636412

Vivid Black - Black Finish

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FLHXSE 2020 CVO™ Street Glide® $40,539.00 $29,999.00

954796

Pre-owned

2020

5760 mi

Harley-Davidson®

Woodstock Harley-Davidson®

1HD1PXL17LB954796

SMKYGRY/BLKHOLE W/PINSTRIPE

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FLHXS 2020 Street Glide® Special $29,999.00 $22,999.00

600364

Pre-owned

2020

6626 mi

Harley-Davidson®

Illinois Harley-Davidson®

1HD1KRP10LB600364

BILLIARD BURGANDY

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FLHTKSE 2020 CVO™ Limited $44,039.00 $29,999.00

952231

Pre-owned

2020

20337 mi

Harley-Davidson®

Windy City Harley-Davidson®

1HD1TEH13LB952231

Moonlight Blue & Deep Sea Blue

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FLHTK 2020 Ultra Limited $28,699.00 $20,499.00

675920

Pre-owned

2020

16493 mi

Harley-Davidson®

Chicago Harley-Davidson®

1HD1KEF12LB675920

Vivid Black - Black Finish

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