As families poured into a converted West Side warehouse Saturday afternoon, Jacob Williams watched small ringlets of his hair tumble to the floor. The rising seventh grader was excited as soon as he spotted the barber chairs, said his mom, who shared that delight when she learned the cut would come free of charge.

Haircuts were just one of the offerings at this year’s Back-2-School Summer Jam, said Tasha Williams, who brought her 12-year-old son to get a free dental cleaning and a few vaccines. Those services, coupled with the day’s celebratory atmosphere, gave her an extra boost of confidence that her son is ready for a new year at KIPP Academy.

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Luna Leos, 6, going into first grade, gets her face painted at a Chicago Teachers Union event that provides free backpacks, haircuts, books and entertainment for children returning to school at the CTU Center in the Near West Side on Aug. 15, 2026. (Arthur Maiorella/Chicago Tribune)

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“You think you know what’s going on and then you come to events like this,” said Williams, 42. “It just opens your eyes to more programs that are available to the community.”

Williams was among hundreds of parents who brought their children to this year’s Summer Jam, which is hosted by the Chicago Teachers Union, ahead of students’ return to the classroom on Aug. 24. The event offered families free supplies as the cost of preparing children for another school year continues to climb.

Educational books and supplies cost about 1.2% more in the average U.S. city than they did last summer, according to federal inflation data. Over the past decade, those prices have risen more than 14%.

Roughly 73% of CPS students were considered low-income last year, according to district data, meaning they or their households received benefits through programs like the Supplemental Nutrition Assistance Program or Temporary Assistance for Needy Families, among other criteria. That need was evident Saturday, organizers said, with more than 800 families registered in advance and hundreds more expected to walk in throughout the day.

For parents like Williams, accessing services in one place can ease the additional strain of scheduling multiple appointments around a full-time job.

“It’s hard to get in to see your doctor, especially right before school starts,” said Williams, who lives in Garfield Park. “Here, we get all of that out the way. It’s a one-stop shop.”

Some kids, like Raeshawn Willis, said their parents couldn’t get time off work to bring them to the event. But the rising seventh-grader still made it, accompanied by his uncle, Chris Brown, who has brought him three years in a row.

As Brown watched his nephew sketch colorful flowers onto a banner in the art room, he said Raeshawn leaves the event more confident about the school year ahead each time he attends. Knowing the Chicago Teachers Union is behind the celebration, rather than an outside community organization, makes the day especially meaningful, he said.

“Having the establishment step up is really cool,” said Brown, 52. “I wish they had something like this for me growing up.”

The event was originally planned for outdoors, organizers said, before the weather forced families to move indoors at CTU headquarters. But aside from a canceled dunk tank, the change of scenery did little to dampen the mood.

Kids with painted faces bobbed along to music from a DJ, breaking only to grab free tacos and ice cream sundaes from local vendors. Others picked out backpacks in their favorite colors and styles, filling them with free crayons and glue sticks.

Of all the resources available Saturday, eighth-grade special education teacher John Conrad was most excited about the tables piled high with free books. Conrad said the event puts physical texts in the hands of students who might otherwise access them only online, giving teachers like him another way to prepare them for the future.

“It’s a reminder of the significance of learning,” said Conrad, 61, who teaches at Madero Middle School in Little Village. “Even though I had some anxiety getting ready for teaching, I’m excited now.”