Chest pain is a relatively common complaint in adolescents and is most often attributed to anxiety or musculoskeletal conditions. Pleuritic chest pain in association with fever and cough are frequently reported in adults with primary pulmonary coccidioidomycosis. We describe three cases in which chest pain mimicking costochondritis was the predominant initial presenting symptom of pulmonary coccidioidomycosis. In addition, in each case, recent tuberculin skin test reactivity complicated the diagnostic assessment and treatment. We conclude that, in endemic areas, coccidioidomycosis should be considered in the differential diagnosis of acute chest pain in teenagers as well as in adults.