Mother-Daughter Team Bringing Sweet Traditions to Chicago

by Region 5 Advocate, Darryl DePriest

According to statistics compiled by the Office of Advocacy, women own over 12 million businesses in the U.S. and employ more than 10 million workers. Two successful women entrepreneurs in Region 5 are the mother-daughter team of Jacqueline “Jackie” and Janel Jackson, who own five Kilwins franchises in the Chicago area.

Ms. Jackson (Jackie) shared, “I like to shop at the Kilwins on South Michigan Avenue, which happens to be less than one hundred yards from the Small Business Administration’s Chicago office.”

Kilwins was started in Michigan in 1947 by Don and Katy Kilwin. It is known for its ice cream, fudge, chocolates, and other sweets, which are handmade. Kilwins now has over 150 franchisee/store owners with stores in 26 states.

Ms. Jackson said that her start in the chocolate industry began in 2007 after the death of her mother. She walked into an ice cream shop and was overwhelmed with memories of getting ice cream with her late mother. “Just the smell of it, everything about it. My mother’s spirit just came over me,” Ms. Jackson recalled. “I knew then this is what I want to do. And the spirit of my mother would live on”.

Ms. Jackson was inspired and opened the first Kilwins ice cream and fudge shops in the Chicago area. The first shop opened in Orland Park, a suburb south of Chicago. She opened the next shop in Old Town, a North Side neighborhood where the Second City comedy troupe is located. Following that, Ms. Jackson convinced Kilwins, which prefers locations in touristy areas, to allow her to open a location in Hyde Park. Hyde Park is her home neighborhood and the home of the University of Chicago.

Ms. Jackson’s path over the past fifteen years has had its share of obstacles. She closed the Old Town location in 2013 after a robbery. She then opened the Kilwins on Michigan Avenue in 2017, a high-traffic tourist area. Ms. Jackson and her daughter, Janel, who became a partner upon graduating from college, were doing well enough that by the Spring of 2020, they were working on opening a Kilwins on Navy Pier, the most visited tourist destination in Illinois. However, events beyond their control interceded.

The first event was the COVID-19 mandates that restricted the operations of many businesses. Since chocolates and ice cream were deemed “nonessential,” their stores were forced to close. Then, in late May 2020, just as the restrictions were about to be lifted the civil unrest that followed the murder of George Floyd resulted in the Michigan Avenue location being looted. Jackie and Janel were not injured, but they ended up spending the entire night in their store to protect it from further damage. Their efforts to pivot to the Navy Pier location were disturbed when the pier announced that it was closing after Labor Day 2020 due to the pandemic and not reopening until Spring 2021.

Nevertheless, with the assistance of the SBA, Jackie and Janel persisted. The Michigan Avenue store was repaired and reopened. Once the temporary closure of Navy Pier ended, the Jacksons opened their store there. However, yet another setback awaited. In November 2021 gunfire on the street outside the Hyde Park location shattered the glass of the storefront. The Jacksons decided to close the store for the remainder of 2021, even though it was the holiday season.

Eventually, the Jacksons decided to renew the Hyde Park lease and remodel the store. They reopened in July 2022. Before the Hyde Park reopening, they took over an existing Kilwins franchise in Geneva, Illinois, another tourist destination located on the bluffs above the Mississippi River. And then in 2023 the Jacksons opened a Kilwins in Andersonville, another North Side neighborhood.

As true entrepreneurs, the Jacksons keep pushing forward. There are plans and a grant from the city of Chicago to build a “chocolate garden” in the back patio of the Hyde Park Kilwins. The renovated area will host up to 200 people for community events, birthday parties, book club events, family reunions, and anything else the neighborhood may need. Ms. Jackson is also trying to develop a Fatburger & Buffalo Express franchise in the Chatham neighborhood on the South Side.

In August 2022 Ms. Jackson penned an essay for Illinois Policy where she summarized her business philosophy:

“There have been a lot of great opportunities that I feel will make a positive impact on the city of Chicago. I am a native of Chicago, and I have so much pride in my city. It’s extremely beautiful. And it has so much to offer.”

“Yet, it’s also a tough time to be a business owner. Wages, cost of goods, construction costs, gas, and transportation have all increased significantly since the pandemic and have really affected my bottom line.”

“I know the taxes for small businesses are also becoming very challenging. I think that is extremely important to press on, especially with all the crime and other business closures because it’s a difficult environment. I decided, despite all the madness, this would be the perfect opportunity to expand and continue the legacy I have started.”

-Jackie Jackson

Darryl DePriest serves as the Regional Advocate for Region 5 covering Cleveland and Columbus, Ohio, as well as the states of Illinois, Indiana, Michigan, Minnesota, and Wisconsin. Please feel free to contact Darryl DePriest at and our other regional advocates to share your small business regulatory burdens or concerns.

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