Jacqueline Jackson Chosen as Illinois Small-Business Person of the Year

Jacqueline Jackson
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In a “bittersweet” career, Jacqueline Jackson’s Small Business Association award is the most recent achievement.
Owner of the Kilwins business Jacqueline “Jackie” Jackson stood in front of glass cases brimming with rich truffles, caramel apples, and nut caramel turtles reminiscent of the ones her late mother cherished in Andersonville.
Following multiple difficult beginnings as the owner of a chain of Kilwins chocolate stores, Jackson’s tenacity was honored on Thursday at an awards ceremony attended by family, friends, and officials.
The U.S. Small Business Administration Great Lakes region honored her the Illinois small-business person of the year. The recipient of the prize, SBA regional administrator Geri Aglipay, described Jackson as a shining example of “resilience, innovation, and entrepreneurial spirit.”

Her journey “is not just one of success, but of triumph over adversity, because like many business owners, she has had her share of setbacks that would have made many people give up,” Aglipay said.

In spite of hurdles, including store break-ins, the pandemic and personal challenges, “she refused to let her dreams go,” Aglipay said.

Jackson joins the ranks of former SBA award winners who were originally tiny businesses but are now well-known national brands, such as Ben and Jerry’s, Callaway Golf, Chobani, Dogfish Head Brewery, Stonyfield Farm, Pacifica Beauty, Maui Brewing Co., and Tom’s of Maine.
During National Small Business Week, the administration presented the award to honor the 33.5 million small companies that power American economies and serve as the backbone of communities.
Illinois has received 543,000 new company applications since 2021, the federal government reports. According to the SBA, companies are launching nationwide at a rate that is 65% quicker than it was before the pandemic.

Jackson owns five Kilwins in the Chicago region. Kilwins is a Michigan-based chocolate and ice cream restaurant that was established in 1947 and currently has locations in about 26 states.
Over ten years ago, Jackson established her first Kilwins in Orland Park. She now has a store in Andersonville, one in Geneva and Evanston, and two downtown locations at Navy Pier and Michigan Avenue. This month, she plans to launch a business in River North. Her workforce has expanded from 10 to over 75 workers. Jackson also intends to launch a Chatham-based Fatburger franchise in June. She was a member of the group that set up a Fatburger at 15110 S. LaGrange Road in Orland Park the previous year.

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