Pain and sleep exhibit a bidirectional relationship, leading to questions about how to prioritize treatment targets. This article illustrates the efficacy of a sleep intervention on functional outcomes for an adolescent with disrupted sleep patterns, chronic migraines, and a complex psychological and social history. Baseline data indicated that the patient’s sleep duration was well below recommendations for adolescents. Migraine headache, as well as fatigue secondary to sleep issues, resulted in missing 1–2 days of school per week. Ferritin evaluation and history of sleep irregularity warranted iron supplementation and actigraphy. Actigraphy data confirmed delayed sleep wake phase disorder (DSWPD), and chronotherapy was initiated. After the initial active chronotherapy phase, the patient maintained a regular sleep schedule and school attendance improved. Preexisting mental health issues remained, but symptoms were described as more manageable. After approximately 5 weeks in the maintenance phase of chronotherapy, drift to increased sleep onset latency was observed. Additional actigraphy data were collected during the maintenance phase, which supported an ongoing need for follow-up through the clinic, including use of other behavioral sleep interventions. This case study illustrates the efficacy of a sleep intervention (chronotherapy) on improving sleep regularity and daily functioning for an adolescent with DSWPD and chronic migraine pain. It also highlights the difficulty implementing this intervention over time, warranting the need for routine follow-up. Future research should focus on how to prioritize treatment targets in patients with comorbid pain conditions and sleep disruptions.