Background: In this study, we aimed to identify factors correlating with satisfaction with orthognathic surgery in order to improve its outcome. Methods: We recruited 77 participants who had received orthognathic surgery and 32 age- and gender-matched normal-controls. Questionnaires that included devised questions for family support, Big Five Inventory, Derriford Appearance Score, Pittsburgh Sleep Quality Index, Hospital Anxiety and Depression Scale, 36-Item Short-Form Health Survey, and a visual analogy scale for satisfaction, were completed before and one month and nine months after the surgery. The statistical analysis methods included descriptive statistics, t-test, and Pearson correlation. Results: All participants received the preoperative and one-month follow-up, while 28 also completed the nine-month follow-up. Satisfaction was not significantly related to demographic data, but long-term satisfaction was related to an extraverted personality. The preoperative and postoperative results of the Derriford Appearance Scale were related to short-term and long-term satisfaction. Furthermore, both the preoperative and one-month postoperative Pittsburgh Sleep Quality Index findings were significantly related to short-term satisfaction. The postoperative 36-Item Short-Form Health Survey was significantly related to short-term and long-term satisfaction. Conclusions: Not only subjective distress and dysfunction of appearance but also sleep problems and quality of life were correlated to satisfaction with orthognathic surgery. In the future, relevant interventions can be developed to further improve patient’s satisfaction and their physical and mental health.