Chylothorax and chylous ascites occur when lymphatic fluid accumulates in the pleural space or peritoneum, respectively. They are classified as either traumatic or non-traumatic, and lymphomas are the most common non-traumatic cause. Lymphomas can obstruct the lymphatic architecture causing lipid-rich chyle to leak out below the level of the obstructing mass. Bilateral chylothoraces presenting in the presence of chylous ascites, secondary to Non-Hodgkin Lymphoma, are rare. We describe a case of a 55-year-old man with recurring large-volume chylous ascites secondary to Non-Hodgkin lymphoma who developed bilateral chylothoraces. Initially, he presented with dyspnea and hypoxia and was found to have bilateral pleural effusions, requiring bilateral thoracentesis for diagnostic and therapeutic management. The fluid removed from the pleural space was found to be lymphatic fluid, and the patient was eventually discharged home with instructions to follow up with oncology for further management. The case reveals a temporal relationship where a huge volume of chylous ascites develops into a chylothorax.