Harley-Davidson® Motorcycles For Sale in Chicago & Milwaukee

Explore the thrilling world of Harley-Davidson® motorcycles at Windy City Motorcycle Company in Chicago & Milwaukee! Our diverse selection of Harley-Davidson® bikes is designed for riders seeking power and style. Whether you're a seasoned rider or new to the scene, we have the perfect Harley-Davidson® motorcycle for you in stock. Visit one of our Harley-Davidson® dealerships today and experience the freedom of the open road on a new Harley-Davidson® motorcycle!
 

Windy City Motorcycle Company Inventory

Showing 1-20 of 1074 results

A Brief History of Harley-Davidson® Motorcycles!

For well over a century, Harley-Davidson® has been one of the leading names in American motorcycle production and it’s not hard to see why. With decades of experience producing dozens of different motorcycles suited to unique riding purposes, Harley-Davidson® has garnered itself a loyal following around the world. Keep reading to learn the fascinating history behind this motorcycle giant! Visit a Windy City Motorcycle Company dealership serving Chicago, IL, Milwaukee, WI or Detroit, MI today to check out our entire selection of Harley-Davidson® motorcycles for sale! We’re proud to serve our friends from across Northern Illinois and Southern Wisconsin!
 

Founded in Wisconsin

Harley-Davidson® was founded in Milwaukee, Wisconsin, by childhood friends William S. Harley and Arthur Davidson in a small garage in 1903. The first item the friends built was a single-cylinder engine that was designed to be added to a simple pedal bicycle, which had only just been developed within the preceding few decades. 

Because the engine was not able to power the bicycle up Milwaukee’s steep hills, the two men tried again to develop a motorized bicycle without pedals. The resulting invention was a motorcycle that swiftly became popular with locals. Soon, Harley-Davidson® was able to build a factory and keep up with high customer demand.
 

Creating a Name

During the ensuing decades, Harley-Davidson® motorcycles were used during World War I and World War II, because the company was able to weather the Great Depression well compared to other motorcycle manufacturers.

The company began to expand its range of motorcycles by tailoring new models to certain uses, including competition, style, long-distance riding, and off-roading. Today, you can choose from a wide variety of different Harley-Davidson® motorcycles that feature classic stylings and advanced features.

Stop by one of our many dealership locations serving Milwaukee, WI, or Chicago, IL, today to view our great selection of new Harley-Davidson® motorcycles for sale. Windy City Motorcycle Company is proud to serve all of our customers throughout Illinois and Wisconsin.