Legendary Harley-Davidson Dealer Group acquires Windy City Motorcycle Company

Windy City Motorcycle Company, the Midwest’s largest Harley-Davidson dealership group, has been acquired by industry veterans Marc Ingwersen and Jerry Carillo of the Legendary Harley-Davidson Dealer Group. The deal represents one of the most significant Harley-Davidson and powersports transactions in recent years, expanding the group’s footprint into the Chicagoland market.

Founded in 2000 by Ozzie and Jill Giglio, Windy City grew from a single Harley-Davidson dealership in Villa Park into a multi-brand, multi-location network representing Harley-Davidson, KTM, and Triumph. Over the past 25 years, the company has established a reputation for strong sales, expert service, and community engagement through dealership events and organized rides to destinations such as Sturgis, Daytona, and Route 66.

“Ozzie and I are grateful to the tens of thousands of riders we’ve met along the way,” said founder Ozzie Giglio. “Marc and Jerry share our passion for riding and the community, and we’re confident they’ll take the Windy City legacy to the next level.”

Ingwersen and Carillo bring decades of dealership leadership experience, with a track record of customer-focused operations and recognition through Harley-Davidson’s Bar & Shield and Premiere Service Awards. Their Legendary Harley-Davidson Dealer Group currently includes Buckeye Harley-Davidson (Dayton, OH), CinCity Harley-Davidson (Cincinnati, OH), High Stakes Harley-Davidson (Florence, KY), and Lucky Peach Harley-Davidson (Atlanta, GA).

“Windy City is an iconic name in the Midwest with a loyal customer base and a strong team,” said Ingwersen. “We’re excited to build on that foundation and expand opportunities for riders in this region.”

The acquisition includes Wild Fire Harley-Davidson, Illinois Harley-Davidson, Woodstock Harley-Davidson, Woodstock KTM & Triumph, Lake Shore Harley-Davidson, Starved Rock Harley-Davidson, and Starved Rock KTM. Current employees are expected to remain in their current positions, with a focus on maintaining continuity of service and community involvement.

For dealers, the move underscores the trend of larger dealer groups expanding their regional presence through acquisition, bringing new resources and strategies to established markets.

Windy City Motorcycle Company: From One Store to Regional Powerhouse

• 2000 – Founded by Ozzie and Jill Giglio with a single Harley-Davidson dealership in Villa Park, Illinois.
• 2000s–2010s – Expanded into multiple Harley-Davidson locations across Chicagoland.
• 2010s–2020s – Added KTM and Triumph franchises, evolving into a multi-brand, multi-dealership network.
• Community Impact – Hosted organized rides to Sturgis, Daytona, Route 66, Bikes & BBQ, and the Great Lakes.
• 2025 – Acquired by Marc Ingwersen and Jerry Carillo’s Legendary Harley-Davidson Dealer Group, marking a new chapter for the Midwest market.

Legendary Harley-Davidson Dealer Group: Building on Community and Growth

• Leadership – Founded and led by longtime industry veterans Marc Ingwersen and Jerry Carillo.
• Dealership Network – Operates Buckeye Harley-Davidson (OH), CinCity Harley-Davidson (OH), High Stakes Harley-Davidson (KY), and Lucky Peach Harley-Davidson (GA).
• Recognition – Multiple Harley-Davidson Bar & Shield Awards and Premiere Service Awards for customer care and operational excellence.
• Community Focus – Known for large-scale dealership events, charity rides, and partnerships that strengthen ties with local riders.
• 2025 Expansion – The acquisition of Windy City Motorcycle Company dealerships adds seven Midwest locations, establishing a strong presence in Chicagoland.