Introduction Migraine, a prevalent condition in Saudi Arabia, is linked to various risk factors, including night shifts. Existing literature, mainly outdated, suggests conflicting findings on the relationship between sleep, night shifts, and migraines. Our study aims to investigate the specific association between shift work and migraine attacks among healthcare workers in the Kingdom of Saudi Arabia (KSA), addressing a notable research gap. Methodology This is a cross-sectional study conducted in Saudi Arabia. Data were collected by using a non-probability convenience sampling technique. Data were collected through an online questionnaire and analyzed using SPSS version 26 (IBM Corp., Armonk, NY). Results Our study on 342 healthcare workers in the KSA revealed the majority of participants were females (70.5%, n = 241), aged between 25 and 29 years (38.9%, n = 133), with doctors being the predominant profession (51.5%, n = 176). Participants had an average of 5.9 years of healthcare experience. Work shifts included rotating (43.3%, n = 148), day (48%, n = 164), evening (3.8%, n = 13), and night shifts (5%, n = 17). Notably, 89.2% (n = 305) experienced headacheswith varying characteristics and triggers. Management strategies included over-the-counter painkillers (56.1%, n = 192) and rest (50.5%, n = 173). Gender was significantly associated with migraines (p = 0.020), while night shift frequency and years in health care showed no significant associations. Higher weekly working hours relate significantly to migraines (p = 0.034). Conclusion Our study highlights a significant association between migraines and gender, with females being more prone. Night shift frequency and years in health care showed no significant associations, while higher weekly working hours were linked to migraines.