In this report, we present the case of a 72-year-old female diagnosed with an aortic dissection variant and bilateral pulmonary emboli (PE) in the setting of Coronavirus Disease of 2019 (COVID-19) infection. The patient was transported from home to the emergency department (ED) via emergency medical services (EMS) with acute chest pain and dyspnea. After arriving at the ED, she was hypoxic on her baseline supplemental O2 requirement and tachycardic and tachypneic. Computed tomography (CT) angiogram of the chest showed evidence of possible thoracic aortic dissection and bilateral PE. The patient was ultimately transported to a tertiary center for operative aortic repair and bilateral embolectomy and, fortunately, survived the procedures. Interestingly, during operative repair of the aorta, no obvious dissection flap was noted, but rather evidence of a limited tear in the intimal layer of the aorta. This is an interesting case as acute aortic injuries in the setting of COVID-19 infection have not been as widely documented as PE in the setting of COVID and highlight the need for further research on the possible association between them.