Background Dry eye disease is a tear film disorder which can cause discomfort to patients and negatively affect vision acuity. A number of risk factors has been reported to affect the incidence and severity of dry eye syndrome (DES). The aim is to study the prevalence of DES in Saudi Arabia and the factors affecting the severity of DES in relation to the use of contact lenses. Methods A cross-sectional questionnaire-based study was conducted on 310 participants using the ocular surface disease index (OSDI) questionnaire and the eye dryness part from contact lens questionnaire-8 (CLDEQ-8). Dry eye OSDI scores were compared across different epidemiological and risk factors with focus on the use of contact lenses. Pearson and Spearman’s correlation coefficients were used to analyze the frequency of contact lenses usage in relation to OSDI scores. Student’s t-test and one-way analysis of variance (ANOVA) tests were used to compare means of two or more than two groups, respectively. Results Forty eight (15.5%) of participants did not have any degree of DES, achieving an OSDI score between 0 and 12. Forty participants (12.9%) scored from 13 to 22, (mild DES), 44 (14.2%) were moderate, scoring 23–32 on the OSDI, while those who scored above 33 were 178 (57.4%) had severe DES. The mean score for all participants was 37.8. A high percentage of participants (84.5%) had some degree of DES. There was a strong positive correlation between OSDI score and the frequency of the feeling of dry eye and a moderate positive correlation between OSDI score and the intensity of dryness feeling. Out of 310 participants, 136 (43.9%) indicated using contact lenses. There was no significant association between the use of contact lenses per se and DES, however, those who used contact lenses more frequently had significantly higher OSDI scores. Conclusions Dry eye syndrome is a widespread, underdiagnosed condition in Saudi Arabia. The frequency of contact lenses use may contribute to the incidence of DES.