A pancreaticopleural fistula (PPF) is a rare complication of chronic pancreatitis secondary to a pancreatic pseudocyst or any disruption of the main pancreatic duct. It commonly presents as a recurrent left-sided pleural effusion after multiple thoracentesis. We present a rare case of a 41-year-old woman with numerous flares of chronic pancreatitis presenting with large bilateral serosanguinous pleural effusions and trapped lung secondary to a PPF. To our knowledge, this is the first documented case of a PPF leading to bilateral pleural effusions resulting in a trapped lung.