Pancreaticopleural fistulas are a rare complication of pancreatitis. We report two cases from our institution and review 37 cases of pancreaticopleural fistulas identified in the literature. Endoscopic retrograde cholangiopancreatography was more sensitive compared to computed tomography in demonstrating pancreaticopleural fistulas (79% versus 43%, respectively). Medical therapy with total parenteral nutrition, octreotide, and/or chest tube placement was successful in resolving the pancreaticopleural fistula in up to 33% of cases. None of the patients who underwent pancreatic duct stent and/or nasopancreatic drain placement required surgical intervention. Endoscopic retrograde cholangiopancreatography is the initial test of choice when the diagnosis of pancreaticopleural fistula is suspected. Early endoscopic intervention with pancreatic duct stent placement is recommended given its high success rate in fistula closure. Medical therapies are useful adjuncts to endoscopic therapy, but rarely result in pancreaticopleural fistula closure alone. Surgical interventions should only be considered after failure of endoscopic and medical therapies.