The present study aimed to investigate the effects of shift work on sleep among pilots and Helicopter Emergency Medical Service crew members (HCM) in the Norwegian Air Ambulance. Sleep was assessed by diaries and actigraphy during a workweek (24 h duty for 7 consecutive days) in the winter season and a workweek during the summer season in pilots and HCM (N = 50). Additionally, differences in sleep were studied between the week before work, the workweek, and the week after work in both seasons. Results indicated that bedtime was later (p <.001) and time spent in bed (p <.05) was shorter during the summer, compared to the winter, season. The workers delayed the sleep period in the workweek, compared to the week before (winter: p <.001, summer: p <.001) and the week after (winter: p <.05-.001, summer: p <.001). They spent more time in bed during the workweek, compared to the week before (winter: p <.001, summer: p <.01) and after (winter: p <.001, summer: p =.37). Further, the workers had longer wake after sleep onset during the workweek, compared to the week before (winter: p <.001, summer: p <.01) and the week after (winter: p <.01, summer: p <.01). Finally, the workers had lower sleep efficiency during the workweek recorded by actigraphy compared to the week before (winter: p <.01, summer: p <.001) and the week after (winter: p <.01, summer: p <.001). According to the sleep diaries the total sleep time was 7:17 h in the winter and 7:03 h in the summer season. Overall, the sleep was somewhat affected during the workweek, with delayed sleep period, longer wake after sleep onset, and lower sleep efficiency compared to when off work. However, the workers spent more time in bed during the workweek compared to the weeks off, and they obtained over 7 h of sleep in both workweeks. Our findings suggest that the pilots and the HCM sleep well during the workweek, although it affected their sleep to some extent.