Commercial airline pilots (CAPs) are a key employee group within the travel industry who are exposed to multi-level institutional and organizational demands that impact their lived experience of stress potentially leading to accidents and incidents. This study explores CAPs’ lived experience of stress and draws on conservation of resources theory and context and travel stage frameworks to investigate unique stressors that CAPs face at different travel stages. Utilizing qualitative data from interviews with 28 CAPs combined with archival data, we surface a range of multi-level factors that impact their lived experience of stress at each travel stage. To cope with stressors, and in the absence of valuable contextual resources, CAPs utilized multiple personal resources. We additionally found evidence of significant spillover across the travel stages. Findings highlight the need to improve contextual resources available to pilots, strengthen their personal resources, and customize support to the requirements of the travel stage.