Portal vein thrombosis (PVT) is a rare vascular disorder with an estimated incidence of 2-4 cases per 100,000 inhabitants. Although chronic liver disease (especially cirrhosis), hepatobiliary malignancies, major infectious/inflammatory abdominal diseases, and myeloproliferative disorders are well-recognized predisposing conditions for PVT, various abdominal inflammatory processes can also predispose to visceral venous thrombosis. In this article, we present a case series of three patients with a clinical diagnosis of acute cholecystitis complicated by visceral venous thrombosis. We describe the clinical presentation, imaging findings, therapeutic approaches-including the use of injectable anticoagulants and direct oral anticoagulants (DOACs)-and the impact of venous thrombosis on the timing of definitive surgical treatment. We also discuss the implications of these findings in the context of current knowledge and propose management strategies for similar cases.