Background: Medical versus surgical management of pediatric periorbital infection secondary to acute bacterial rhinosinusitis (ABRS) can be a dilemma for clinicians. This study aimed to evaluate the prognostic factors related to the need for surgical drainage and to help direct management decisions. Methods: Children admitted for periorbital infection secondary to ABRS between 2001 and 2019 were retrospectively reviewed. Demographics, clinical presentations, laboratory data, comorbidities, and computed tomography results were collected from medical records. Results: A total of 141 pediatric patients were enrolled. Forty-two patients (29.8%) required surgical intervention. Multivariate logistic regression analysis identified that delayed initiation of intravenous antibiotics from the onset of periorbital swelling (odds ratio [OR] = 1.94; p < 0.001) and proptosis at initial presentation (OR = 6.63; p = 0.008) were significantly associated with the need for surgical intervention. A C-reactive protein value of > 55.73 mg/L and initiation of intravenous antibiotic treatment > 2 days from the onset of periorbital swelling showed the best predictive power for surgery. Conclusion: Pediatric patients with delayed initiation of intravenous antibiotic treatment and initial presentation of proptosis had worse outcomes and required surgical intervention.