Chicago Back-2-School Event Supports Families with Free Services

At a bustling converted West Side warehouse, families arrived for the Back-2-School Summer Jam on Saturday afternoon. Jacob Williams, a rising seventh grader, watched as small ringlets of his hair fell to the floor. Excitement was clear when he discovered free barber services, his mom related. Haircuts were amongst numerous services offered, as Tasha Williams took her 12-year-old son for a free dental cleaning and a few vaccines. The day’s lively atmosphere bolstered her confidence that he was ready for the new year at KIPP Academy.

Luna Leos, age six, enjoyed having her face painted at a Chicago Teachers Union event. The gathering provided free backpacks, haircuts, books, and entertainment for kids returning to school Aug. 15, 2026, at the CTU Center in the Near West Side, captured by Arthur Maiorella of the Chicago Tribune.

Jacob’s participation was part of a larger group of parents taking advantage of the Summer Jam, hosted by the Chicago Teachers Union. As students prepared to return on Aug. 24, the event offered families free supplies amidst rising school preparation costs. According to federal inflation data, educational book and supply prices were 1.2% higher this summer compared to last, having increased over 14% over the past decade.

Given that about 73% of CPS students were labeled low-income last year based on the district data, and the assistance offered Saturday was crucial. More than 800 families were pre-registered, with many more expected to attend throughout the day.

For parents like Williams, accessing multiple services in one location relieved the burden of scheduling separate appointments around a full-time job. “Getting into see your doctor is tough, especially as school starts,” said Williams, from Garfield Park. “Here, everything’s settled; it’s a one-stop shop.”

Some children, like Raeshawn Willis, didn’t have parents able to take them. Yet, he arrived alongside his uncle, Chris Brown, attending for three consecutive years. Brown noted Raeshawn’s increased confidence about school as he sketched colorful flowers onto a banner. He acknowledged the significance of the Union backing the event rather than an external community group.

“Having the Chicago Teachers Union involved is meaningful,” stated Brown, age 52. “Such resources weren’t available when I was growing up.”

Initially planned for outdoors, event organizers shifted based on weather concerns, moving families indoors to CTU headquarters. Despite the canceled dunk tank, spirits remained high. Kids with painted faces danced to DJ music, only pausing for free tacos and ice cream from local vendors. Others selected backpacks, filling them with crayons and glue sticks.

Among available resources, eighth-grade special education teacher John Conrad showed enthusiasm for tables stacked with books. “Physical texts in students’ hands are significant,” said Conrad, 61, teaching at Madero Middle School in Little Village. “It’s a reminder of why learning matters, easing the stress of teaching prep and exciting for the future.”