Several randomized controlled trials have implemented cognitive behavioral therapy for insomnia (CBT-I) for patients with comorbid insomnia and chronic pain. This systematic review and meta-analysis investigated the effectiveness of CBT-I on patient-reported sleep, pain, and other health outcomes (depressive symptoms, anxiety symptoms, and fatigue) in patients with comorbid insomnia and chronic non-cancer pain. A systematic literature search was conducted using eight electronic databases. Upon duplicate removal, 6374 records were screened against the inclusion criteria. Fourteen randomized controlled trials were selected for the review, with twelve (N = 762 participants) included in the meta-analysis. At post-treatment, significant treatment effects were found on global measures of sleep (standardized mean difference = 0.89), pain (0.20), and depressive symptoms (0.44). At follow-up (up to 12 mo), CBT-I significantly improved sleep (0.56). Using global measures of sleep, we found a probability of 81% and 71% for having better sleep after CBT-I at post-treatment and final follow-up, respectively. The probability of having less pain after CBT-I at post-treatment and final follow-up was 58% and 57%, respectively. There were no statistically significant effects on anxiety symptoms and fatigue at either assessment point. Future trials with sufficient power, longer follow-up periods, and inclusion of CBT for pain components are warranted.