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Transforming Kilwins: The Success Story of Jacqueline Jackson

Stepping into the Kilwins in the heart of Hyde Park, patrons are immediately greeted by the scent of fresh chocolate and smooth sounds of neo soul. Jacqueline Jackson, who owns the franchise at 5226 S. Harper Ave. along with six other shops in the city, said she styled the confectionery to be an inviting and safe space for neighbors. A winning strategy, as it turns out. Earlier this month, after more than 16 years running the candy and ice cream parlors, Jackson was named the Small Business Administration’s Illinois small-business person of the year.

The award, she told the Herald in an interview, is a major milestone in a rocky road to success. A former Chicago Public Schools teacher and realtor, Jackson opened her first Kilwins franchise in 2008 in Orland Park. She was inspired to open a chocolate shop a few years after her mother’s death, when she stumbled into a Kilwins on a whim and was immediately comforted by the scene of chocolate. Reminded of her mother, Jackson said she realized she wanted to do something more purposeful.

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Later that year, when the financial crisis came, she closed this location and moved her shop to Old Town. “I didn’t give up – I packed my bags and moved to another location,” she said. But problems arose at this shop too: the Old Town store was robbed several times. So she set her eyes on Hyde Park, where 53rd Street was undergoing a University of Chicago-led revitalization project.

Jackson said no bank would give her a loan to open a shop there, but she found a friend in the U. of C.’s office of commercial real estate. With support from family and financial assistance from the U. of C. she expanded to Hyde Park in 2012, and later to stores in downtown Chicago and at Navy Pier.

But after a shooting outside her Hyde Park store in November of 2021, Jackson closed the shop indefinitely to take a mental health break. At that time, she recalled, she thought she might never open the store again.

The shooting happened just after noon on a Tuesday. Luckily, her store was unexpectedly closed that morning due to a scheduling error for daylight savings time. Though a stray bullet shattered one of the shop’s windows, nobody was inside.

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