Background: Pancreaticopleural fistula is a rare complication of chronic pancreatitis resulting from pancreatic duct disruption, typically presenting with pleural effusion and predominant respiratory symptoms. Bilateral pleural involvement is exceptionally uncommon and poses significant diagnostic and therapeutic challenges. Case Presentation: A 56-year-old man with a history of chronic alcohol abuse presented with progressive dyspnea and mild epigastric pain. Imaging revealed bilateral pleural effusions, an atrophic pancreas with a markedly dilated main pancreatic duct containing calculi, and a fistulous tract extending from the pancreatic body through the esophageal hiatus into the mediastinum. Magnetic resonance cholangiopancreatography confirmed the diagnosis of chronic calculous pancreatitis complicated by a pancreaticopleural fistula. After unsuccessful conservative management, the patient underwent distal pancreatectomy, resection of the fistulous tract, and Roux-en-Y pancreatojejunostomy. The postoperative course was uneventful, with complete resolution of pleural effusions and sustained clinical improvement. Conclusions: This case highlights the importance of considering pancreaticopleural fistula in patients with unexplained pleural effusions and minimal abdominal symptoms, particularly in the context of chronic pancreatitis. Bilateral involvement, although rare, should not preclude timely diagnosis. Appropriate diagnostic studies by computed tomography, magnetic resonance imaging, and magnetic resonance cholangiopancreatography are crucial for establishing the diagnosis. Surgical management offers definitive treatment in patients with ductal obstruction and calculous disease, resulting in excellent long- term outcomes.