Chronic pain is defined as pain that persists following tissue injury or disease processes and is believed to have taken place after healing. It is a functional impairment that causes discomfort and leads to the inability to perform various essential daily activities. Chronic pain in pediatrics can be of various types, the most commonly prevalent types being headaches, abdominal pain, and limb pain. Adolescents with chronic pain have been found to have generalized anxiety scores twice that of the average population, along with significant impairment of family dynamics. Some forms of chronic pain respond effectively to medication and psychotherapy, and recurrence is common when stress is triggered by external or environmental factors, most recently in the form of COVID-19. In this case series, we discuss three cases of worsening mental health presentations and chronic pain exacerbation in the context of the COVID-19 pandemic. We talk about the unique perspective of chronic pain in the pediatric population and comorbid mental illnesses and their management from a psychiatric standpoint.