Background: The career choice of specialization in the medical profession is very complex. This study aimed to observe the most popular specialty of medical specialization, factors influencing the student's choices, and future job features that would impact the choice of medical specialty and the career choice. Methods: A cross-sectional study was conducted in 2022 through a self-administered online survey, distributed by email, through the office of clinical affairs, to the final year (6th year) medical students and interns in seven different medical schools in the Western Region of Saudi Arabia. Results: A total of 294 participants completed the survey, of which 56.5% were 6th-year medical students. The gender distribution of the sample was almost 2:1 female to male ratio. The most common choice of field specialization was surgical subspecialty followed by emergency medicine at 16.0%, and 15.6%, respectively. The items that had the most impact on the medical students' choice for medical field specialty were: love of the specialty (57.0%), followed by attending a rotation in the chosen field (43.8%). Future job features that had a major impact in choosing the field of specialization were: wanting to work in a large city hospital (38.6%), followed by the ability to have time to pursue other non-medical interests (31.7%). Conclusion: The most popular specialty chosen was a surgical subspecialty, by both sexes, followed by emergency medicine. The most influencing personal factor was the love of the field, and the most influencing future job feature was to work in a large city hospital.