Obstructive Sleep Apnea (OSA) is a partial or total upper airway collapse resulting in sleep-breathing disturbances. There are many medical comorbidities associated with OSA; hence, this study is important as the prevalence of patients with medical comorbidities associated with OSA is increasing. The study aimed to correlate medical comorbidities and OSA symptoms of the patients along with their upper airway dimensions using Cone Beam Computed Tomography (CBCT) scans to identify patients at risk of developing OSA. This cross-sectional study included patients who had CBCT imaging taken between 2014 and 2020. A questionnaire was used to gather information on patients’ medical history and OSA symptoms. The upper airway dimensions of the CBCT scans were evaluated before logistic regression and Fisher’s exact test were carried out to determine the relationships between the variables. p ≤ 0.05 was considered statistically significant. Logistic regression revealed an association of longer length (p = 0.016), smaller total volume (p = 0.017) and width (p = 0.010) of upper airways with hypertension. Furthermore, loud snoring was seen in patients with hypertension, heart disease and obesity whereas difficulty concentrating during the day was present in subjects with deviated nasal septum, tonsillitis and depression. For upper airway dimensions, a smaller average volume was associated with loud snoring (p = 0.037), difficulty concentrating during the day (p = 0.002) and mood changes (p = 0.036). A larger anterior-posterior dimension was also associated with excessive daytime sleepiness (p = 0.042), difficulty concentrating during the day (p < 0.001) and mood changes (p = 0.009). Longer airway length was additionally found to be associated with loud snoring (p = 0.021). CBCT taken for dental investigations could be correlated with patients’ medical history and OSA symptoms to screen patients at risk of OSA.