Background: Communication skills (CS) learning is a core skill in medical and dental education. The comparison of attitudes towards CS between dental and medical students based on the taught curriculum (problem-based learning vs. traditional teaching) in Saudi Arabia awaits investigation. Aims: (1) To assess the attitudes of both undergraduate dental and medical students towards communication skills (CS) learning and (2) to compare the attitudes towards CS between Medical and Dental students in relation to sociodemographic and education-related characteristics. Methods and Materials: A cross-sectional study, using an online survey, invited 260 conveniently sampled Taibah university medical and dental undergraduate students. The survey collected data on sociodemographic characteristics, education-related factors, and CS using Communication Skills Attitude Scale (CSAS) that assess positive and negative attitudes (PAS, NAS). Data analysis included descriptive statistics and the Mann–Whitney U test. Results: Of the distributed questionnaire 91% responded (145 dental and 91 medical students). There were, overall, non-significant scores’ differences between medical and dental students on PAS (Medicine Median 51 vs. Dentistry Median 50, p = 0.059) and NAS (Medicine Median 32 vs. Dentistry Median 32, p = 0.596). Older medical students, those at clinical levels and those who reported they need to improve their communication skills and student whose parents were not doctors, tended to score statistically significantly (p = 0.032, 0.017, 0.034, and 0.004, respectively) on PAS compared with dental students; on the other hand, medical students with doctor parents scored significantly high in NAS compared to dental students (p = 0.015). Conclusion: Demographic and education-related characteristics underpinned medical student positive attitude towards CS compared to dental students. Although medical and dental students showed no differences in self-rating their attitudes towards (CS). Different factors influence medical and dental students’ attitudes towards CS learning.