Windy City Motorcycle Company, one of the largest Harley-Davidson dealership groups in the Midwest, has been bought by “legendary” leaders Marc Ingwersen and Jerry Carillo, owners of Legendary Harley-Davidson Dealer Group. While the ownership is changing, the mission remains the same. This sale marks a new era for the Midwest motorcycle market, notes Windy City founder Ozzie Giglio. “It will build on Windy City’s legacy of excellence in motorcycle sales, service and community engagement.” Terms of the sale were not announced.
“Windy City Motorcycle Company was built with passion and a deep respect for the riding community,” explains Giglio. “Marc and Jerry share that same passion, and I couldn’t think of a better group to lead this Midwest motorcycle dealer network into the future.”
Founded in 2000 by Ozzie and Jill Giglio, Windy City Motorcycle Company began as a single point Harley-Davidson dealership in the Chicago suburb of Villa Park, created by riders for riders. Over the past 25 years, it has grown into a multi-dealership/multi-brand company with a strong regional presence, offering riders across the Midwest access to leading motorcycle brands, expert service and a vibrant community of enthusiasts. The dealerships included in this transaction are Wild Fire Harley-Davidson, Illinois Harley-Davidson, Woodstock Harley-Davidson, Woodstock KTM and Triumph, Lake Shore Harley-Davidson, Starved Rock Harley-Davidson and Starved Rock KTM.
Marc Ingwersen and Jerry Carillo are seasoned professionals with decades of experience in the powersports industry. They are best known for their leadership in dealership operations and dedication to rider-focused business practices. With this acquisition, Ingwersen and Carillo bring a strategic vision for innovation, growth, and continued customer satisfaction. “Windy City Motorcycle Company is an iconic name in the Midwest, known for its incredible team, loyal customers, and commitment to the motorcycle lifestyle,” Ingwersen expressed his enthusiasm for the opportunity. “We are excited to build on that legacy and explore new ways to serve riders with the quality and care they’ve come to expect.”
The transition is expected to be seamless, with current employees remaining in place. Under Ingwersen and Carillo’s leadership, the company will continue its focus on high quality service, expansive inventory, and community involvement, while also exploring new growth opportunities across the region.
About Windy City Motorcycle Company
Windy City Motorcycle Company is a leading powersports dealership group based in Chicago, Illinois, representing Harley-Davidson, KTM and Triumph. Established in 2000 by Ozzie and Jill Giglio, the company operates multiple locations across the Midwest and offers a wide range of motorcycle brands, services, parts and apparel. With a reputation for excellence and a deep connection to the riding community, Windy City continues to be a top destination for motorcycle enthusiasts.
Windy City has hosted multiple tours across the United States and destinations such as Sturgis, Route 66, Daytona Bike Week, Bikes & BBQ and tours around the Great Lakes. Ozzie and Jill sincerely thank the tens of thousands of riders they’ve met and befriended over the past 25 years, and look forward to more time on the road on their two wheels with the best customers in the world. They’re confident that this acquisition will help the Chicagoland market even more and can’t wait to support the next leadership.”
About Legendary Harley-Davidson Dealer Group
Led by Marc Ingwersen and Jerry Carrillo, The Legendary Harley-Davidson Dealer Group brings decades of dealership expertise and a proven track record that includes multiple Bar & Shield Awards as well as Gold & Silver Premier Service Awards reflecting a consistent commitment to customer care and operational excellence. Known for large-scale community events, charity rides and partnerships that strengthen local connections, the Legendary Harley-Davidson Dealer Group has built a reputation for combining professionalism with genuine passion for motorcycling.
For Ingwersen and Carrillo, the dealerships are more than showrooms—they are gathering places where riders and families come together, friendships are built and adventures begin.
Its family of dealerships include Buckeye Harley-Davidson in Dayton, Ohio; CinCity Harley-Davidson in Cincinnati, Ohio; High Stakes Harley-Davidson in Florence, Kentucky; and Lucky Peach Harley-Davidson in Atlanta, Georgia. With the addition of the Windy City Motorcycle Company dealerships in the Chicagoland area, the organization is broadening its reach while keeping community, culture, and the rider experience at the center of everything it does.
