For these Chicago moms, college scholarships for their kids meant a scholarship for them too: ‘It’s never too late’

Lara Romero vividly remembers the first time she attended college nearly two decades ago, having just given birth to her first child, Salvatore, soon after graduating high school. It took Romero nearly a decade to finish the two-year associate’s program at City Colleges of Chicago.

Those 10 years were plagued with stress about the cost, pressure to prioritize motherhood and long days without a babysitter. Some days, she brought Salvatore to class and asked a professor to watch him while she took notes.

After eight years, Romero, 38, enrolled in college again last fall — at the same time as her son.

This time, Romero enrolled at National Louis University with the hope of becoming a nursing clinical instructor. Salvatore, now 19, started his freshman year at the University of Illinois to study data science and geography.

The Romero family represents a rising number of parents attending college and earning degrees at the same time as their children through a local organization that fully funds college scholarships for two generations at once.

Scholarships for parents and their kids make longtime dreams a reality.

“I was a little nervous about going back to school, but it’s something I’ve always wanted to do,” said Lara Romero, who lives in the Pilsen neighborhood with her three younger children.

For the Romeros, navigating college simultaneously is an unusual experience.

They are similar to college roommates, texting each other good luck messages before exams. And similar to high school friends, Lara and Salvatore Romero visit each other as much as they can during the school year.

“I’ll tell him, ‘Hey, I have a test this morning.’ And he’ll be like ‘you got this Mom,’” Lara Romero said.

More than 130 parents have entered postsecondary education or workforce programs since 2022 through scholarships provided by Hope Chicago, a local nonprofit that supports two generations of families with scholarship money raised by private donors.

Launched in 2021, the scholarship program funds college tuition, room and board, food assistance and a stipend for any high school graduate of the five partner Chicago Public Schools.

About 1,200 CPS students have pursued advanced degrees through the program. When students enroll, their parent automatically becomes eligible for a scholarship to pursue a degree or certification at a partner higher education institution.

For April Kilgore-Wooden, a 50-year-old mother of five in Morgan Park, that meant her dream of teaching in a classroom could become a reality.

In 2021, Kilgore-Wooden was driving when she found out her daughter Lauryn’s high school was one of five Chicago Public Schools eligible for the scholarships. Immediately, she felt the opportunity was more than a free education — it could be life-changing.

“I heard the radio make the announcement that it was Morgan Park … and I was so overwhelmed just knowing that someone is investing in me and my child, first and second generation,” Kilgore-Wooden said. Out of her five children, Lauryn will be the first to obtain a degree.

When Lauryn, 18, enrolled as a first-year student at Loyola University Chicago last fall, her mother enrolled at National Louis University to study early childhood education.

Like her mother, Lauryn has known since high school her dream job: to pursue medical school and become a hematologist. As Lauryn spoke about her future profession, her mother jumped in that she had the goal “since she was 2 years old.”

With a year of school under her belt, April Kilgore-Wooden called her daughter her “accountability partner” on a recent afternoon, detailing how the two navigate degrees and going to college.

“With both of us trying to reach the same goal, it makes us both accountable,” April Kilgore-Wooden said. “It’s hard to keep pushing her when I haven’t obtained that goal, so that’s why I’m rushing and I’m hurrying up taking more classes and more classes trying to reach the finish line, so that I can obtain that goal.”

Hope Chicago CEO Janice Jackson said it is a “novel” approach because the model is the largest effort in the country to provide multigenerational scholarships.

Jackson, who was CEO of CPS from 2017 to 2021, said investments in two generations of families felt like the “missing piece” in addressing educational inequities and narrowing the wealth gap in historically underfunded school communities.

What separates the program is the focus on parents with children near adult age, rather than parents with infants, according to Jackson.

“Oftentimes when you think about two-generation models, it’s the parent with a young child, so like we’re gonna teach them how to read or cook together. But we don’t pay enough attention to the relationship that parents have with their children when their children are on the precipice of adulthood,” Jackson said.

A study by the Urban Institute found that mothers in the United States who returned to school and completed a degree earn on average three times more and have better mental health than their counterparts who did not return to school.

The research also found that their biological children were more likely to complete high school, have gains in verbal and reading scores and were about twice as likely to enroll in college, regardless of the child’s age.

“The bottom line is that it yields economic payoff for the entire family,” said Theresa Anderson, author of the study and principal research associate at the Washington, D.C.-based institute.

Data on parents with kids — or parent students — is limited, as research on the demographic did not gain traction until around 2010, Anderson said. Previous research in the 1980s and 1990s was primarily focused on parenting skills and ways to bring in income, not on obtaining postsecondary education, Anderson added.

In 2016, roughly 21% of undergraduate students in Illinois had dependent children, according to the National Postsecondary Student Aid Study. It’s unclear what age their children were.

It wasn’t until 2021 that Illinois became the second state in the country to require schools to record parenting status for its students.

Since then, increased state legislation has shown that parent students — who are more likely to be women and students of color — are now a target priority group for education systems, Anderson said.

About 13% of students attending postsecondary school in the United States either part or full time in 2021 were age 35 years or older, according to data collected by the National Center for Education Statistics. But researchers predicted that number to grow by another 100,000 students by 2024.

When selecting high schools for the program, Hope Chicago identified district schools where the “need was the greatest,” Jackson said. Those schools tended to have low enrollment trends and a lack of financial and wraparound services for students after graduation.

The program partners with schools on the West and South sides of Chicago that have predominantly Black and Latino student populations.The five schools are Morgan Park High School; Benito Juárez Community Academy in Pilsen; Al Raby School for Community and Environment in East Garfield Park; Noble Johnson College Prep in Englewood; and Farragut Career Academy in Little Village.

Through the scholarship, students can attend their choice of more than two dozen schools, including any public school in Illinois and a handful of private schools. Meanwhile, parents have the option of several two- and four-year degree programs, vocational programs, or job training classes, also in the Chicago area or Illinois.

For many parents in Chicago on scholarship, returning to school meant returning to a classroom for the first time since high school while continuing to work the same jobs they built careers in.

Kilgore-Wooden, who has dyslexia, recalled a point in her first year when she considered quitting her teaching program as the stress of navigating college courses and professors, coupled with her learning disability and her main job, almost made her quit the program.

“It wasn’t easy in the beginning and I actually was very frustrated,” she said. “Especially at my age because you haven’t been like educated in a while so you’re kind of like OK, what does any of this mean?”

Now, with the start of her student teaching on the horizon, Kilgore-Wooden plans to graduate in eight months and hopes to work in a CPS school one day soon teaching the district’s youngest children.

“Becoming a teacher was my childhood dream,” Kilgore-Wooden said. “And now I can look forward to becoming an educator.”

Other parents are taking time in retirement to pursue a completely new career path.

Shelia Moore, 56, of Morgan Park, completed a lengthy career in the utilities industry before recently retiring. But the mother of seven children said she now has aspirations to enter a new phase of life and one day pilot an airplane.

Her daughter Dominique, 21, studies biology in her third year at Chicago State University and plans to attend medical school, while Sheila Moore will earn a certificate in aviation mechanics from Olive-Harvey College.

As her mother spoke about her aspirations to one day earn her pilot’s license and fly a plane, Dominique smiled next to her.

“I would tell other parents that it’s never too late,” Shelia Moore said. “Start out small and then by the time their children will be growing up, they’ll be able to go to college right there with them.”

Dominique chimed in with support: “It’s never too late.”