Back-2-School Summer Jam Provides Free Supplies and Services for Chicago Families
As families entered a West Side warehouse on Saturday, Jacob Williams watched as his hair was trimmed. Jacob, a rising seventh-grader, was thrilled when he saw the barber chairs. His mother, equally delighted, was pleased to learn the haircut was free. This was just one of the attractions at this year’s Back-2-School Summer Jam, explained Tasha Williams. She brought her 12-year-old son for a complimentary dental cleaning and a few vaccinations. These services, along with the event’s festive atmosphere, gave her more confidence that her son is ready for the new academic year at KIPP Academy.
Young Luna Leos, aged 6 and starting first grade, enjoyed getting her face painted. This took place at a Chicago Teachers Union event that offered free backpacks, haircuts, books, and entertainment for children returning to school. The event was hosted at the CTU Center in the Near West Side on August 15, 2026.
Williams, who attended with hundreds of other parents, noted the event was enlightening. “You think you know what’s available, and then you come to events like this,” she said. It showcased additional community programs she wasn’t aware of. The Chicago Teachers Union hosts the Summer Jam annually, offering families free supplies, which is increasingly important as the cost of preparing children for school rises. According to federal inflation data, educational books and supplies are 1.2% more expensive than last summer. Over the last decade, prices have climbed over 14%.
In Chicago Public Schools (CPS) last year, around 73% of students were considered low-income. Many families, who received benefits through programs like the Supplemental Nutrition Assistance Program, took advantage of the event’s offerings. Organizers reported more than 800 families registered in advance, with additional walk-ins expected throughout the day.
For parents like Williams, having access to multiple services at one location simplifies scheduling, especially around the demands of a full-time job. “It’s hard to see your doctor right before school starts,” said Williams, who lives in Garfield Park. “Here, we handle all of that. It’s a one-stop shop.”
Raeshawn Willis, a rising seventh-grader, attended with his uncle, Chris Brown, as his parents couldn’t miss work. Brown, who has brought him to the event for three consecutive years, observed his nephew grow more confident about the upcoming school year each time he attends. Brown noted the significance of the Chicago Teachers Union organizing the event, saying it makes it more special. “Having the establishment step up is really cool,” said Brown, 52. “I wish this existed when I was growing up.”
Weather initially forced the event indoors at CTU headquarters. Despite a canceled dunk tank, the mood remained lively. Kids with painted faces danced to music from a DJ, taking breaks for free tacos and ice cream sundaes from local vendors. Others selected backpacks and filled them with free crayons and glue sticks.
John Conrad, an eighth-grade special education teacher, expressed excitement about the abundance of free books. He highlighted the importance of providing physical texts to students who might otherwise access them only online. This initiative gives teachers like Conrad another tool to prepare students for the future. “It’s a reminder of the significance of learning,” said Conrad, 61, who teaches at Madero Middle School in Little Village. Though he had some anxiety about preparing for teaching, the event renewed his excitement.