Families arrived at a repurposed West Side warehouse on Saturday afternoon for the Back-2-School Summer Jam. Jacob Williams, a soon-to-be seventh-grader, watched his hair fall during his free haircut. Jacob’s mother was thrilled, knowing the trim came at no cost. Haircuts were among various services offered at the event.
Tasha Williams, Jacob’s mother, took advantage of additional services like complimentary dental checkups and vaccinations. She felt reassured that these preparations readied her son for KIPP Academy. The event, hosted by the Chicago Teachers Union, aimed to support families before schools reopened on August 24. Luna Leos, a first-grader, enjoyed face painting and free school supplies.
“Events like this open your eyes to community programs,” Tasha Williams noted. Hundreds of parents attended, utilizing opportunities to save on school-related expenses. The cost of educational materials rose by about 1.2% compared to the previous summer, with a 14% increase over the past decade. These rising costs impact many, as 73% of CPS students were considered low-income.
More than 800 families preregistered, with many more expected throughout the event. For parents such as Williams, consolidating services at one location simplifies coordination around work schedules. “It’s challenging to see your doctor right before school begins,” Williams remarked.
Raeshawn Willis, another attendee, was unable to come with his parents due to their work commitments, but his uncle Chris Brown brought him along. Brown, who accompanied Raeshawn for three years, emphasized the confidence these events instilled in his nephew. Knowing the initiative came from the Chicago Teachers Union added significance for many attendees.
Although weather moved the event indoors at CTU headquarters, the lively atmosphere persisted. Kids enjoyed music, snacks, and choosing backpacks. John Conrad, a special education teacher, celebrated the availability of free books. Conrad emphasized the educational importance of physical books for students, beyond digital access.
“It highlights learning’s importance,” said Conrad, preparing for a new teaching year at Madero Middle School. The event energized him despite initial nervousness. Such gatherings not only assist with school readiness but also foster community support and optimism among attendees.

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