Chesterfield Awning Co.: A Legacy of Craftsmanship

A legacy built over generations

Since 1958, Chesterfield Awning Co. has built a reputation around craftsmanship, experience, and service. Founded by two lifelong friends who wanted to build a business of their own, Chesterfield has operated in the region for more than six decades.

Its history reaches even further. Over the years, Chesterfield has acquired several companies whose roots in the Chicagoland awning industry date back to the late 1800s. Those businesses helped shade the storefronts, homes, and institutions of generations throughout Chicago and the surrounding region.

“We’ve consolidated that craft, that experience, and that institutional knowledge into one company,” says Chesterfield President Solomon Abdella.

Today, Chesterfield is a full-service manufacturer of custom fabric and metal structures, serving residential and commercial customers across Chicagoland, northwest Indiana, and parts of Wisconsin and Michigan. Its clients include homeowners, global brands, restaurants, hotels, amusement parks, airports, schools, universities, hospitals, churches, production facilities, and government offices, as well as architects, construction firms, developers, and property managers.

Chesterfield’s offerings include awnings, motorized retractable systems, louvered pergolas, architectural canopies, vestibules, enclosures, standing-seam structures, and more. The company also provides comprehensive design, installation, cleaning, storage, repair, and maintenance services.

Production Manager Steve often says, “If you can dream it, we can build it.” That philosophy reflects the craftsmanship and ingenuity that have enabled Chesterfield to create complex, one-of-a-kind structures for customers throughout its history.

A new chapter for an established business

Before becoming president of Chesterfield, Solomon built his career in finance and consulting. That background helped shape his approach to business ownership.

He began looking for an established lower-middle-market business with a strong reputation and an opportunity to grow through a refreshed business strategy.

In 2025, Solomon had the opportunity to begin conversations with Chesterfield’s previous owner about acquiring the business. As those discussions progressed, he began speaking with several financial institutions about financing the transaction.

For Solomon, the opportunity was about building on what Chesterfield had already established while preparing the company for its next stage of growth.

“Acquiring Chesterfield is a tremendous responsibility I welcomed. This is a company with over 65 years of history, and you're inheriting its legacy: employees, craftsmanship, and reputation with suppliers and customers across Chicagoland and beyond who've trusted them for decades. My goal is to honor that by being thoughtful about every step forward — leaning into growth and value creation without ever losing what has allowed the business to endure for over 65 years,” Solomon says.

Finding a financing partner that understood the vision

As Solomon evaluated potential financing partners, Centrust Bank stood out for its understanding of his plans for Chesterfield and the level of personal attention its team provided.

Solomon says Tom and the Centrust team demonstrated a strong understanding of the vision from the beginning and delivered the personalized, hands-on service he was looking for.

That support continued throughout underwriting, closing, and after the transaction was completed. Solomon credits Tom and team members with remaining accessible and responsive throughout the process.

“We’re extremely grateful for the partnership that Centrust is able to provide,” Solomon says. “They are always accessible and ready to support.”

Looking ahead, Solomon sees that partnership as an important part of Chesterfield’s future.

“We’re excited to partner with Centrust in this new chapter of growth as Chesterfield thinks about the next 50-plus years of business,” he says.

Building Chesterfield for the next generation

Solomon describes Chesterfield as being in the early stages of several initiatives designed to strengthen the business.

The company has an experienced team with an average tenure of more than 10 years, an established reputation across the Midwest, and strong relationships with its supplier network. Solomon sees those strengths as an important foundation for the company’s growth plans.

Current priorities include revamping Chesterfield’s go-to-market approach, enhancing the customer experience, identifying opportunities to improve the employee experience, and updating internal processes and systems.

Hiring is another priority, with plans to add team members across several functions as the company expands its capabilities.

Continuous improvement remains central to the strategy. Chesterfield is looking for ways to strengthen the experience for customers and employees while building on the craftsmanship and institutional knowledge that have defined the business for generations.

The goal is to position Chesterfield for its next 50 years and beyond.

Advice for other business owners considering financing

For business owners exploring financing, Solomon recommends starting with a clear strategy for how the funds may support the business.

Preparation matters, too. Organizing financial statements, growth plans, and other relevant documentation may help business owners communicate their business story clearly during the financing process.

Above all, Solomon encourages owners to be transparent and collaborative with their financing partner.

“You don’t need to have all the answers,” he says, adding that candid conversations with a lender may help business owners understand the reasoning behind the financing process and how lenders evaluate potential borrowers.

Obtaining financing may feel daunting for those who do not come from a finance or consulting background, Solomon says, but transparency and collaboration may go a long way toward creating a productive relationship between a business owner and their financing partner.

For Chesterfield, financing was one part of a broader plan: honor the craftsmanship that built the company, strengthen the experience for customers and employees, and carry an enduring Chicagoland business into its next chapter.

Explore Chesterfield’s custom fabric and metal structures at  ChesterfieldAwnings.com.