Data analysis by Thomas Wilburn
This story was created in collaboration with the Chicago Tribune. Editor’s note: Please do not republish.
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Karen Calloway is always hunting for more ways to bring in dollars for Kenwood Academy.
In recent years, the principal has rented out the South Side high school’s campus to churches, nonprofits, and sports leagues, and leaned on a new parent group to drum up donations. The effort to supplement what the school receives directly from Chicago Public Schools has paid off.
Kenwood spent $418,983 in outside money in fiscal year 2025, compared to a low of about $90,000 in 2021, according to an analysis by Chalkbeat and the Tribune.
At Kenwood, a predominantly Black high school where about half of the students are low-income, that funding has paid for athletic equipment and uniforms, student clubs and college tours.
“Regardless of the budget, as a principal, you should want to create other arms of revenue for your school,” Calloway said. “It’s being flexible and being nimble about how you use the funding that you have.”
Private fundraising has long been seen as a way to pad school budgets in wealthier communities, usually to pay for nice-to-haves, such as field trips and student clubs. But as the district grapples with growing financial woes, more Chicago schools have leaned on parent fundraising, rental income, cell tower revenue, and more to pay for essentials, including staffing.
In fiscal year 2025, district-run campuses spent a total of $48 million in independently raised revenue, the Chalkbeat and Chicago Tribune analysis found. That’s up 78% since 2021, when the district was newly flush with federal pandemic relief.
In an email, a district spokesperson said the total spent in fiscal year 2025 was $51.8 million, but could not explain the discrepancy.
North Side schools have remained dominant in bringing in this outside funding, but some higher-poverty South and West Side campuses such as Kenwood increasingly held their own. Across the city, principals say they appreciate the boost, even as they note playing landlord and overseeing fundraisers can siphon time away from efforts to improve instruction.
The district made some cuts to school budgets this spring to chip at a $732.5 million deficit, under pressure from billions in long-term debt and pension liabilities, aging infrastructure and state funding that remains short of what Illinois deems “adequate.”
“The district’s budget is getting close to the breaking point, so principals are hustling around for additional revenue, the district’s hustling around to buy additional savings and the long-term revenue sources are kind of tapped out,” said Nelson Gerew of the Chicago Public Education Fund.
Larger schools say this funding is a lifeline
Until recently, Amundsen High School spent fundraised dollars on computer carts, classroom materials, and other nonessentials.
A decade ago, about 90% of Amundsen’s students were from low-income families and almost 60% were Latino. Then came an all-out effort to attract more families from the school’s well-to-do Lincoln Square neighborhood. The successful push has been a boon for Amundsen’s reputation and enrollment. It has also meant tighter budgets.
In 2024, the school — where roughly a third of students are now low-income and nearly half are white — lost federal dollars it used to receive for serving a high concentration of disadvantaged students. That year, CPS also adopted a new funding formula that, among other things, guaranteed minimum staffing for a growing number of campuses with smaller student bodies — the culmination of yearslong efforts to steer more resources to needier schools.
Facing a growing budget shortfall, Amundsen spent $894,000 in outside money in 2025, including fundraising, cell tower income, and grant revenue, for operational expenses such as partial staff salaries. That’s roughly 5% of its budget.
“We aren’t using [fundraising] because our kids need iPad 10s instead of iPad 9s,” said Bob Farster, a longtime Local School Council representative. “This isn’t frivolous. We’re not using it for things that aren’t 100% necessary.”
Historically in Chicago, parent fundraising has been a story of have versus have-not schools, a dynamic threatening to drive deeper inequity in a segregated district. Indeed, “Friends of” groups at the city’s premier selective enrollment schools, which tend to serve whiter and wealthier student bodies than the district as a whole, can pull in hefty amounts. Take Friends of Payton, which raised $786,000 for Walter Payton College Preparatory High School in 2023-24, according to the organization’s most recent tax filings, more than any other school in the district.
But the picture has become more nuanced.
Amid the funding shifts, school leaders, LSC members and parent groups at larger high schools like Amundsen — often in wealthier areas but drawing diverse student bodies — say outside revenue is helping to bridge budget gaps, paying for staff positions, pressing building repairs or other essentials.
Without independent revenue, one North Side principal who requested anonymity to speak candidly said, “I can’t make the numbers work.”
At about 1% of total campus budgets in 2024-25, this type of income that schools raise independently of what the district provides is still a small fraction of school spending overall. But it’s growing, and it accounts for a larger portion on some campuses, including 6% at Lincoln Park High School, the highest among CPS schools. This school year, 77 teacher and staff positions districtwide were funded through independent revenue, up from 67 in 2024-25.
Securing independent revenue can be time-consuming and uncertain, school leaders say. Renting out parking lots, auditoriums, and other school facilities often involves coming in on weekends and troubleshooting issues with vendors throughout the week, the North Side principal said.
Meanwhile, high-needs campuses on the South and West sides are stepping up their own fundraising.
Schools serving more low-income families hope to boost outside dollars
At Kenwood’s eighth grade graduation in the school’s courtyard earlier this month, graduates, parents and family members flocked to a booth piled high with “spiritwear”: $45 sweatshirts, $20 baseball hats, $10 tote bags, all with the school’s insignia rendered in ornate lettering. A winding line formed by the booth, manned by members of Friends of Kenwood.
RyAnn Nelson-Jaiyesimi, a 1998 graduate, held up a blue T-shirt with “alumni” scripted across the chest. She walked away with two for $20 each, adding that supporting the fundraiser was an easy decision: “We have kiddos from all different backgrounds, so I definitely think it’s important to give back.”
Ramona Burress, a parent and former head of Kenwood’s Local School Council, helped revive the school’s parent fundraising group at the height of COVID, as many families struggled with access to food, housing, and technology needed for remote learning. Families kept it going after the pandemic’s fallout eased — and after Burress’ three children all graduated from Kenwood.
More recently, Burress joined an informal network of CPS “Friends of” group leaders, dominated by wealthier North Side schools where fundraising is “a well-oiled engine.” In a group chat and in-person meetings, she has gotten tips and ideas for how Kenwood could step up its fundraising efforts, such as a mini-grant competition to support student clubs and sports teams. Burress said the push has also spurred parent engagement at the school and sent a message to students that families and staff care about improving their experience.
At $55,000 last year, the group’s haul is still a fraction of what wealthier schools can raise. It’s also only about 13% of what Kenwood spent in outside revenue last year, income dominated by rental dollars. But the group wants to do more, tapping a network of loyal alumni and local businesses.
“The district is navigating real financial pressures,” Burress said. “Organizations like ours can help to close the gap. Ideally, we shouldn’t have to be here, but we recognize the need.”
The Chalkbeat/Chicago Tribune analysis showed Kenwood and other South and West Side schools serving higher-poverty student bodies have significantly increased the amounts of independently raised revenue in their budgets in recent years, often pulling a mix of rental, cell tower, student fee, and some fundraising income. Dyett High School for the Arts in Washington Park, Corliss High School in Pullman and Benito Juarez High School in Pilsen are among the 80 campuses on the South and West Sides that have tripled their outside spending dollars since 2021.
Overall, this type of spending went up by 40% at South and West Side schools since 2021 and accounted for almost a third of the total amount of independently raised revenue schools across the city spent.
In some cases, outside revenue has allowed such campuses to offer extras that have long been staples at wealthier schools. But increasingly, even as the district has shifted its funding model to prioritize higher-need campuses, some school leaders on the South and West Side say outside revenue has also helped shore up their budgets.
Gunsaulus, a Southwest Side magnet school serving largely low-income Latino families, spent a growing amount of cell tower revenue in recent years. Meanwhile, the school’s parent fundraising arm, Amigos de Gunsaulus, held an annual raffle to pay for field trips in the United States and South Korea all students take. But the group has also recently stepped up its efforts to raise more for campus needs, such as school supplies and arts programs.
Amigos has worked to adapt to its more limited fundraising prowess. Amigos used to host “dressdown” days, when parents could chip in $1 so their student wouldn’t have to wear the school uniform. But, says Vanessa Espinosa, the group’s president, Amigos did away with the practice because it felt unfair to low-income families.
The group has instead tried to emulate the annual fundraising galas and walkathons wealthier schools host, except its members target the school’s teachers and local businesses instead of their families — an approach that helped Amigos raise $166,000 in 2024-25, according to tax filings.
“We are conscious that our community has many limitations,” Espinosa said.
Increasingly, district leaders are noticing these schools’ fundraising efforts.
District officials push schools to get creative in raising revenue
In a district presentation the week school budgets were released this spring, principals were urged to tap any available dollars in the special funds containing parent fundraising, rental, and other revenue before appealing their staffing allocations.
The district has also more recently encouraged schools to rent out their facilities when possible and started taking a cut. Officials say this new “facility fee” helps offset some of CPS’ growing building maintenance expenses. The district said it will raise the fee for some schools this summer “to more accurately reflect actual building operating costs.” Schools hosting cell towers keep a third of that revenue; CPS redistributes the rest to all campuses, the district said.
A CPS spokeswoman told Chalkbeat and the Tribune that it takes a hands-off approach to school efforts to generate revenue independently and has a “neutral stance” on parent fundraising.
“While fundraising can play a role in finances at the local school level, it will not compensate for the nearly $3 billion in COVID-related funding allocated to CPS,” the district said in a statement.
Still, district officials have shown some interest in helping higher-poverty schools step up their game when it comes to securing outside revenue.
At Kenwood, Burress says she has met twice with the head of the regional office overseeing Kenwood and other high schools about replicating the school’s fundraising efforts on other South Side campuses. School board members have voiced interest as well. Gunsaulus’ Espinosa has also gotten inquiries from a network administrator and principals at nearby schools to present on launching a fundraising nonprofit without a pricey attorney.
Lauren Sartain, one of the authors of a 2023 Federal Reserve Bank of Chicago study of CPS fundraising, cautions against relying too much on independently raised revenue.
“To think you can tap these dollars to support all students who have needs is simply not realistic,” Sartain said.
Still, school leaders and advocates said that they are grateful for these dollars — even more so amid this spring’s budget cuts. At Whitney Young, a coveted selective school on the Near West Side, Friends of Whitney Young money once supported building improvements and student groups. But this year, for the first time, the nonprofit will fund two teaching positions.
Friends of Whitney Young president Patricia Herrera put it simply: “We’re basically a lifeline now.”
Mila Koumpilova is Chalkbeat Chicago’s senior reporter covering Chicago Public Schools. Contact Mila at mkoumpilova@chalkbeat.org.
Kate Armanini is the education reporter at the Chicago Tribune.
Editing by Becky Vevea, Corilyn Shropshire, and Mónica Rhor; data analysis by Thomas Wilburn; visual presentation by Steve Rosenberg, Todd Panagopoulos and Susan Gonzales; engagement design by Ellen Przepasniak and Caroline Bauman; copy editing by Mónica Rhor and Robert Loerzel.
Editor’s note: This story was created in collaboration with the Chicago Tribune. Please do not republish.