Introduction: The choice of medical specialty depends on several factors, such as gender. There is an unequal distribution according to gender among health professions, in medicine specialties are also unequally distributed. There are no recent studies on the national situation. Objective: To analyze the association of gender as a variable in the choice of medical specialties in Chile between 2020 and 2022. Materials and Methods: Cross-sectional study with data from those who entered specialties by Destination and Training Stage (EDF) or National Competition for Entry to the National Health Services System (CONISS) between 2020 and 2022. Sex was compared with the mechanism and year of entry, the specialty, and its modality. Results: The sample included 2.759 applicants (49% women and 51% men). Women were found mostly in non-surgical specialties and with shifts (p < 0.001), while men were found in greater proportion in surgical specialties and with shifts (p < 0.001). Traumatology, neurosurgery and urology were the specialties with the highest proportion of men, while pediatric family medicine, geriatrics and pediatrics had a majority of women. Discussion and Conclusion: We found an association between sex as an independent variable and the choice of medical specialties in Chile between 2020 and 2022. Factors such as lifestyle, work-life balance, social status and sociocultural barriers may influence the choice of a medical specialty. There are marked differences in the sex/specialty ratio in some medical specialties.