Spontaneous bilateral chylothorax and chylous ascites rarely develop in conjunction with systemic venous thrombosis, and the most common cause of non-traumatic chylous effusion is a malignancy. A 23-year-old immunocompetent female presented with a fever of 5 months' duration associated with progressive shortness of breath and abdominal distension. Evaluation revealed bilateral chylothorax, chylous ascites, and multiple venous thrombosis. Anti-tubercular drugs were initiated on the basis of a lymph node biopsy and computed tomography findings, but her symptoms worsened, and she developed massive bilateral pleural effusions with type 2 respiratory failure requiring invasive mechanical ventilation. She was managed with anti-tubercular drugs, chest tube drainage, octreotide, anticoagulants, and other supportive treatments. A multipronged approach to the management of chylous effusions and addition of octreotide led to resolution of symptoms. The challenges faced in diagnosing and managing this case are discussed in this report.