Endoscopic balloon dilation (EBD) is an effective method for treating stricture-related obstruction in Crohn's disease. We aimed to identify factors predictive of successful avoidance of surgery, including endoscopic features, in patients undergoing balloon dilation. We performed a retrospective review of patients with symptomatic Crohn's disease-related intestinal strictures undergoing EBD. Clinical, medication use, laboratory, and dilation data, including the minimum and maximum balloon sizes used, and number of balloons used per endoscopic session were collected. Multivariate analysis by Cox proportional hazard regression was used to model future surgical bowel resection. In a total of 135 subjects undergoing 292 dilations, multivariate modeling demonstrated that failure to achieve a maximum dilation of 14 mm or more increased the risk of surgery (hazard ratio [HR] 2.88, 95% confidence limit [CL], 1.10-7.53). Although there was no difference in the risk of future surgery between maximum EBD sizes of 14 to 15 mm and 16 to 18 mm, those reaching 16 to 18 mm exhibited a longer interval between subsequent dilations (mean 240 ± 136.7 versus 456 ± 357.3 d, respectively, P = 0.023). Endoscope passage at index dilation was not predictive of future surgery (HR 0.63, 95% CL, 0.31-1.26). Adjusting for covariates of EBD size, stricture location and type, a C-reactive protein >1.5 mg/dL (HR 2.60, 95% CL, 1.12-5.94), and anti-tumor necrosis factor initiation after index EBD (HR 2.39, 95% CL, 1.09-5.25) increased the risk of future surgery. Although dilation calibers larger than 14 to 15 mm were not more protective against future surgery, those reaching 16 to 18 mm underwent maintenance dilation less frequently. The risk of surgery associated with post-EBD anti-tumor necrosis factor initiation suggests that effective therapy is often used too late in the disease course.