Windy City Ribs & Whiskey and Dockside Delivery

Terri Evans Website
Food & Beverage
South Loop/Douglas, Chicago, IL
Services utilized:
Group Coaching, Loans

Entrepreneurship—and whiskey—runs in Terri Evans’ blood. Terri’s great-grandfather, born a slave, became a renowned business owner in 1865 after the abolition of slavery. He created wealth for his family through land ownership and selling whiskey. Today, Terri continues her family legacy with her two business ventures: Windy City Ribs & Whiskey and Dockside Deliveries.

In 2018, Terri purchased Windy City Ribs & Whiskey in Chicago’s South Loop neighborhood, initially as a side hustle alongside her full-time corporate job. By 2019, it became her full-time passion.

Under her ownership, Windy City Ribs & Whiskey opened a second location at Navy Pier. Until the pandemic hit, her business was thriving.

“It was an amazing first year off the ground,” said Terri. “Then when the pandemic hit, the whole entire floor of Windy City started to fall apart because we were so dependent upon the conventions and the arena.”

Terri questioned how to stay afloat, but she soon found her answer when her friend invited her on a chartered yacht.

“There was no opportunity to get food out to the harbor,” Terri said. “We had a restaurant that needed to drive food sales and we had employees that needed to work, so it was a perfect combination that happened during the pandemic.”

From there, Dockside Delivery was born. Dockside Delivery caters food and liquor to charter services at 31st Street Harbor as well as the other Harbors in Chicago.

In 2023, with the help of an A4CB small business loan, Terri was able to purchase a food container allowing her to have a physical presence at 31st Street Harbor.

“It was my understanding that I was going to be able to get a loan through a traditional bank,” said Terri, but days before the container’s delivery, the loan agreement fell through and Terri found herself in need of quick funding.

“I was in a really tight position, so I will forever be grateful for Allies [for Community Business] for having this micro loan available for me,” she said.

In the fall of 2023, Terri participated in A4CB’s Neighborhood Entrepreneurship Lab where she worked with business advisors to grow her two businesses. “Taking a deep dive into the numbers and figuring out how to become bankable were key for me,” said Terri. “But the community and ability to pick up the phone and ask for advice, to me, that is priceless.”

Terri now leads a team of 12 year-round staff and five seasonal staff. Looking forward, she hopes to continue in her great-grandfather’s footsteps by expanding Dockside Delivery across the country and opening additional locations for Windy City Ribs & Whiskey.