Introduction: Self-medication is a growing public health concern worldwide. Studies have shown a gap between best practice and the current practice of using over-the-counter (OTC) medications. Despite being a well-recognised problem in Saudi Arabia, few studies have investigated OTC medication use in Saudi Arabia. Therefore, this study aimed to investigate the attitudes and knowledge of parents regarding OTC medication use in the Jeddah region, Saudi Arabia. Method: A cross-sectional study was carried out via an electronic questionnaire sent randomly to parents over four months, from 1 January to 30 April 2022. The participants’ characteristics and categorical variables were represented descriptively by frequency and percentage. A Chi-square test was used to test the relationship between the variables. Results: In total, 211 questionnaires were included in this study. Females represented 54.5% of the participants included in the study. Parents belonging to the 18-to-30-year-old group comprised the highest percentage (37.9%), and most of the parents (72.9%) had received an undergraduate education. Family physicians were the most common source (37.3%) of information about OTC medications, whereas more than half of parents purchased OTC medications from the community pharmacy (58.8%). While almost half of the parents (52.1%) visited a family physician when side effects of OTC medications appeared in their children, only (33.6%) stopped giving their children the OTC medicine. The relationship between the sociodemographic characteristics (including educational level, marital status, and employment status) and OTC drug consumption was significant (p < 0.001). Conclusion: Educational campaigns are needed to guide patients about the proper use of OTC medications. Studies on OTC medication use are lacking in Saudi Arabia in terms of its frequency, reasons for use, type of self-medication, and contributing factors.