Terri Winfree has played a part the past 25-plus years managing and improving the role of business. Now she’s stepping back as she relinquishes her latest duties as president of the Chicago Southland Chamber of Commerce.
She accepted the job as a part-time one-year position in 2020, but she stayed for nearly five years.
“I care about the chamber, and I thought this would be good, this would be fun. And I have enjoyed it. It’s been fun. You get to be creative,” she said. “Being that I’d served on the (chamber’s) board for so many years, and I’ve been around, so I knew that, and I knew the potential and knowing the region you know who to contact, so that was helpful.”

The Chicago Southland Chamber of Commerce is a business organization, but it works collaboratively with many organizations, such as the South Suburban Mayors and Managers Association, Visit Chicago Southland (formerly known as the Chicago Southland Convention & Visitors Bureau) and regional chambers. It stretches from the Illinois-Indiana state line west into southwest communities in Cook and Will Counties.
“I call it a member organization instead of a business association, though if someone was to look it up, its more referred to as a business association,” she said, “especially its past history.”
This year the chamber marks 90 years. It originated as the Harvey Businessmen’s Chamber. That evolved into the South Suburban Chamber and now the Chicago Southland Chamber of Commerce.
Membership today is “everybody and anybody,” Winfree said. The chamber’s structure allows for varied interests and the group will host topic-specific lectures and programs to draw people in.
The chamber also acts as a helping agency to provide businesses information from state, county and local agencies. The chamber was especially busy during the pandemic sharing information on government benefits.
“We’re connecting the dots, if you will, working with the Southland Development Authority, Cook County and other sources. We are sometimes a conduit. I call myself a connector bringing people together,” she said.
One of her initiatives was the chamber’s hosting a musical program in downtown Flossmoor featuring performances by Illinois Philharmonic Orchestra members. The first concert was during COVID when the IPO didn’t have a season and people weren’t supporting businesses because of health restrictions.
Today the Flossmoor Chamber Night has expanded and is drawing a crowd from outside of Flossmoor.
“That was bringing people together for a free concert and the community benefits,” she said. The event gives a good vibe in the community. Winfree calls it “a win-win.”
Winfree’s first foray into business started at a restaurant more than 25 years ago. She decided the restaurant’s accounting system needed an update, so she went to Prairie State College to gain skills that would help computerize the system.
“And then I stayed,” she said. “I enjoyed learning.” Winfree worked in the PSC computer lab.
She enrolled at PSC and earned an associate’s degree and then a bachelor’s degree and a master’s degree from Governors State University. She went on to earn a doctorate degree from Colorado State University. It seemed with each degree, Winfree got a new position at PSC — manager, director, associate dean, dean — before becoming the college’s president in 2013. She served as the chief executive for seven years.
During her PSC tenure, she was involved with the Chicago Southland Chamber of Commerce.
Winfree is looking for a change of pace. She won’t give up her part-time teaching jobs at GSU and elsewhere. She’ll keep running the Illinois Community College System Foundation in Springfield and continue as co-president for the Illinois Community College Board.
But for a time, Winfree won’t be available. She’s decided to travel through Europe. She’s calling it “Terri’s Epic Adventure.” It will serve as a type of sabbatical. She has one goal on the trip. She’ll be raising money for scholarships for each of the 500 miles she walks on the El Camino pilgrimage trail in Spain.