Aortic dissection most often is an acute event dominated by excruciating pain and other symptoms which suggest the diagnosis. Our report and a review of the medical literature demonstrate that chronic aortic dissection may, rarely, present as a prolonged febrile illness, with night sweats, weight loss, pleural effusion, and little or no pain. These symptoms may be associated with a markedly elevated erythrocyte sedimentation rate (ESR), anemia of chronic disease, and hyperglobulinemia. Awareness of this unusual presentation, a high index of suspicion, and confirmation by an appropriate imagine technique (CT or MRI of the chest or transesophageal echocardiography have a very high sensitivity) will result in earlier diagnosis and better patient outcome.