There is limited evidence on the standard care for painful obstructive chronic pancreatitis (CP), while comparisons of endoscopic and surgical modes for pain relief have yielded conflicting results from small sample sizes. We aimed to obtain a clear picture of the matter by a meta-analysis of these results. We searched the Pubmed, Embase, and Cochrane Library databases to identify studies comparing endoscopic and surgical treatments for painful obstructive CP. Pooled effects were calculated by the random effect model. Primary outcomes were overall pain relief (complete and partial), and secondary outcomes were complete and partial pain relief, complication rate, hospitalization duration, and endocrine insufficiency. Seven studies with 570 patients were included in the final analysis. Surgical drainage was associated with superior overall pain relief [OR 0.33, 95% CI 0.23–0.47, p < 0.001, I2 = 4%] and lesser incidence of endocrine insufficiency [OR 2.10, 95% CI 1.20–3.67, p = 0.01, I2 = 0%], but no significant difference in the subgroup of complete [OR 0.57, 95% CI 0.32–1.01, p = 0.054, I2 = 0%] or partial [OR 0.67, 95% CI 0.37–1.22, p = 0.19, I2 = 0%] pain relief, complication rates [OR 1.00, 95% CI 0.41–2.46, p = 0.99, I2 = 49%], and hospital stay [OR −0.54, 95% CI −1.23–0.15, p = 0.13, I2 = 87%] was found. Surgery is associated with significantly better overall pain relief and lesser endocrine insufficiency in patients with painful obstructive CP. However, considering the invasiveness of surgery, no significant differences in complete or partial pain relief, and heterogeneity of a few parameters between two groups, endoscopic drainage may be firstly performed and surgical drainage may be considered when endoscopic drainage fails.