Harley-Davidson® Motorcycles For Sale in Chicago, IL & Milwaukee, WI

Enjoy the latest Harley-Davidson® motorcycles from Windy City Motorcycle Company dealerships! We offer the widest selection of new motorcycles for sale and are sure to have the models you need in stock. Don't wait to stop by our Harley-Davidson® motorcycle dealers serving Chicago, IL all the way up to Milwaukee, WI, and learn more about the latest bikes. If you don't see the Harley-Davidson® bike you've been looking for in our current inventory, reach out to our team to see if we can find it for you! We have a wide network of Harley-Davidson® dealerships, and can often find the bike our customers have been looking for! 
 

Windy City Motorcycle Company Inventory

Showing 1-20 of 1289 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.