Pancreaticopleural fistula is an extremely rare complication of chronic pancreatitis with characteristic feature that it may appear in the absence of changes of acute pancreatitis. We present a case of a 32-year-old man whose CT scan showed multiple pseudocysts along the body and tail of the pancreas, left crus of diaphragm and in the posterior mediastinum with associated splenoportal thrombosis. MR cholangiopancreatography imaging diagnosed the case as a pancreatico-pleural fistula, with the fistulous tract connecting distal body and tail of the pancreas to the posterior mediastinum through a diaphragmatic hiatus with right-sided mild-to-moderate pleural effusion. Meanwhile the patient was treated conservatively for his acute symptoms that included pleural tap also. Finally, endoscopic retrograde cholangiopancreatography was done and minor papilla papillotomy was performed and a stent was placed. Knowledge about such cases would help one to be aware of such a rare but dangerous complication, so that timely and correct diagnosis and management can be undertaken.