Triumph Motorcycles For Sale in Chicago, Detroit & Milwaukee

Hit the road and get an adrenaline rush with the latest Triumph motorcycles from Windy City Motorcycle Company! We're proud to be your home for Triumph motorcycles in Chicago, Milwaukee, and Detroit. Our new Triumph bikes are built for speed, handling, and angling out on an open road. Stop by to take a tour of one of our Triumph motorcycle showrooms today!

Windy City Motorcycle Company Inventory

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*Financing Offer available only on select new, untitled 2022 and 2023 Harley-Davidson® Grand American Touring and Adventure Touring motorcycles financed through Eaglemark Savings Bank and is subject to credit approval. Touring models Road King® Special, Electra Glide® Highway King, Road Glide® Special Anniversary, Street Glide® Special Anniversary and Ultra Limited® Anniversary are excluded. Harley-Davidson CVO™, Trikes, Icons Motorcycle Collection, and Police Duty Motorcycles are excluded. Not all applicants will qualify as the Annual Percentage Rate (APR) will vary based on the applicant's past credit performance and the term of the loan. Financing offer is available only for up to a 48-month term. For example, a 2023 Street Glide® ST motorcycle in Vivid Black with Black Trim with an MSRP of $29,999, no down payment and amount financed of $29,999, 48-month repayment term, and 1.99% APR results in monthly payments of $650.70. In this example, customer is responsible for applicable taxes, title, licensing fees and any other fees or charges at the time of sale. APR is calculated according to the simple interest method. Not valid in conjunction with other offers. Customer must take delivery by March 31, 2024. This Financing Offer is valid during the period of February 1, 2024, to March 31, 2024. Other terms, conditions, and limitations may apply. Dealer participation may vary. Financing offer is subject to change or cancellation at anytime. See your Harley-Davidson® Dealership for details.

**$1,000 or $2,000 incentive valid for in-dealership purchase of Genuine Harley-Davidson® Parts & Accessories and/or Apparel & Licensed merchandise in connection with the purchase of select Grand American and Adventure Touring Motorcycles valid at participating Harley-Davidson® dealerships within the continental U.S. and Alaska. Offer valid toward the purchase of select new, untitled 2022 or 2023 Harley-Davidson® Grand American Touring or Adventure Touring motorcycles available and in stock at participating H-D® dealers between February 1, 2024 and March 31, 2024. Offer may not be available in all states. Touring models Road King® Special, Electra Glide® Highway King, Road Glide® Special Anniversary, Street Glide® Special Anniversary and Ultra Limited® Anniversary are excluded. Harley-Davidson CVO™, Trikes, Icons Motorcycle Collection and Police Duty Motorcycles are excluded. Offer cannot be redeemed for cash or cash equivalent. Offer is subject to change at any time without notice. Void where prohibited or restricted by law. Dealer participation may vary. Additional restrictions apply, see your Harley-Davidson® Dealership for details.

The History Of Triumph Motorcycles!

Dating back to the very origins of the motorcycle, Triumph has been a leading brand in the industry for over a century. Many, including several celebrities like Steve McQueen, have found that the British-born company creates just the right bike to fit their needs. Triumph is a name long associated with high performance and reliability, and one ride is all you’ll need to see why. To help you learn more about the history of this illustrious company, read Windy City Motorcycle companies history of Triumph Motorcycles. We are proud to serve our friends from Northern Illinois and Southern Wisconsin!
 

Early Days

Before 1902, Triumph Cycle Co. Ltd. was mainly known for making sewing machines and bicycles. That all changed when its factory in Coventry, England produced its first motorcycle. Resembling little more than a bicycle with a small, single-cylinder Belgian Minerva engine attached to it, it was nevertheless the start of something great. 

Triumph soon began producing its own engines as well, and in 1905 became a part of the nascent competitive motorcycle racing scene. This meant producing a more powerful 450 cc engine, but Triumph was up to the task. From such a humble start, production soon rose to up to a thousand motorcycles every year before 1910.
 

Joining The War Effort

When the World Wars struck its native Britain, Triumph was far from idle. During the first World War, it supplied the Allied forces of Europe and the United States with reliable and fast motorcycles, making battlefield transport far easier. This was a role it would play again in the Second World War. Tragically, Coventry became a target for wartime bombing, and in 1940, Triumph’s factory was among the many buildings destroyed by the heavy bombing. 

Triumph was quick to rebuild and resume its wartime contributions. In 1942, the company built a new factory in Meriden, England. Between then and the war’s end in 1945, Triumph produced over 40,000 motorcycles for military usage. 

Entering The U.S. Market

Though Triumph had already been exporting their motorcycles to the US for years, the formation of the American-based Triumph Corporation allowed the company to sell more bikes there than anywhere else in the world. 

World War II veterans who had ridden Triumph bikes on the battlefield remembered the name and eagerly bought them when they returned to civilian life, knowing that they could expect power and reliability from the Triumph name. This reputation was bolstered when in 1953 actor Marlon Brando rode a Triumph 650cc Thunderbird 6T in the movie The Wild One. This helped cement motorcycles as a fast, affordable alternative to cars in the American consciousness.
While popular among everyday folks, Triumph also enjoyed great success in the racing circuit. Triumph motorcycles were a common sight, though one you might miss if you blinked at the wrong time. Indeed, Triumph bikes sometimes reached speeds of nearly 200 miles per hour! 

Though the brand went through some difficulties in the 1970s and 80s, what emerged after all the restructuring was a company ready to carry the legacy of Triumph motorcycles into the next millennium and beyond. To this day, Triumph maintains its dedication to producing high-performance and high-quality motorcycles at decent prices. 

We here at Windy City Motorcycle Company hope that this history lesson on Triumph Motorcycles has taught you a little about the company and what you can expect from their bikes. To view our selection of Triumph models, visit us at one of our fifteen dealerships across Northern Illinois and Southern Wisconsin. Our staff is always happy to answer your questions, so come on by from Milwaukee, WI, Chicago, IL, or Detroit, MI!