Varicella-zoster virus (VZV) infection can rarely present with severe vascular pathologies, such as deep vein thrombosis (DVT) and pulmonary embolism (PE). These events are seldom documented in the literature as complications of primary VZV infection in adults. We present the case of a 52-year-old Caucasian male patient with chickenpox complicated by DVT and PE, which developed despite thrombectomy and anticoagulation. Laboratory analysis revealed elevated antiphospholipid antibodies. Although the patient was discharged home after clinical improvement, antiphospholipid antibodies remained elevated on repeat bloodwork eight weeks later. Our case report is followed by a literature review of 16 prior cases documenting primary VZV infection followed by DVT, PE, or both. The sex distribution of these cases, including ours, had a male-to-female ratio of 15:2. Mostly, DVT and PE occurred in the first and second weeks, underscoring the critical importance of screening for subtle thrombotic symptoms and risk factors for thrombosis during active VZV infection. Additionally, an argument can be made for ensuring the constant availability of the chickenpox vaccine for individuals with an increased baseline thrombotic risk, even if countries decide not to include varicella vaccination in their national immunization programs.