This study aims at evaluating and categorizing patients’ objective and subjective postoperative recovery symptoms after bimaxillary orthognathic surgery assigning the healing process. The patients were monitored throughout the recovery process, and their symptoms were managed. A prospective, observational study was performed. Patients with Class II and III malocclusion (aged 18 to 35) were evaluated and monitored preoperatively, and postoperatively at 48 h, 2 weeks, 1 month, and 3 months postsurgery. A questionnaire was used to assess pain and anesthesia/hypoesthesia. The most common objective and subjective signs that were correlated with the healing process were edema, hematoma, trismus, pain, and anesthesia/hypoesthesia. Edema peaked at 48–72 h postoperatively (distance between eye’s external canthus and gonion, mean difference = 4.53, between tragus and cheilion, mean difference = 7, between tragus and gnathion, mean difference = 4.65, p < 0.001); mouth opening amplitude was significantly decreased during the first two weeks postsurgery (class II, mean difference = 32.42, p = 0.006, class III, mean difference = 44.57, p < 0.001), but it steadily and considerably improved over three months. The nose tended to widen postsurgery. The most severe pain experienced by patients was of medium intensity in the mandibular body, described as pressure, and usually did not spread. Patients were most severely and persistently impacted by anesthesia/hypoesthesia.