Introduction Headache is a considerable factor in decreased productivity and work efficiency. This study aims to measure the characteristics of headaches and the risk factors among healthcare providers in Al-Ahsa, Saudi Arabia. Methods This cross-sectional study included 353 healthcare providers from Al-Alhsa, Saudi Arabia. An online questionnaire was conducted to assess the demographic and occupational characteristics, headaches, numerous factors such as smoking, caffeine intake, physical activity, and medical conditions to determine their associations with headaches, as well as the impact of headaches on productivity. Results Among participants who reported headaches, 15.6% and 4.5% had been previously diagnosed with tension headaches and migraines, respectively. The mean duration of headaches was 7.09±18.16 hours; 38.5% of headaches were throbbing in nature, while 61.5% were pressing. The headache was on one side in 51.6% and accompanied by nausea and vomiting in 41.1% and 24.1%, respectively. Moreover, 53% and 41.9% experienced worsening of headaches by exercise and light, respectively. Tension headaches occurred more in older healthcare providers (P <0.05) and those who reported working night shifts (P=0.002). Healthcare providers with tension headaches reported having an intrusive leader and violence at work (P=0.038 and P=0.013, respectively). Caffeine consumption, emotional stress, and using oral contraceptive pills (OCP) were significantly correlated with migraine (P=0.023, P=0.017, and P=0.004, respectively). The reported headache affected the productivity of 62.59% of individuals. Conclusions Headache is common among healthcare providers in Al-Ahsa, Saudi Arabia. The study indicates that tension headache is associated with aging, night shifts, having an intrusive leader, and violence at work. In contrast, migraine is correlated with caffeine consumption, emotional stress, and OCP use. The productivity of healthcare providers is affected negatively by headaches.