Synchronous lung and esophageal carcinomas are rare clinical entities. Curative resection with lymph node dissection is the most optimal treatment approach for both tumors. However, due to the high potential risk of postoperative complications, the right approach is to make a patient-specific decision via a multidisciplinary approach at all stages. In this article, we present three cases of synchronous lung and esophageal tumors treated with different approaches due to their specific circumstances and discuss their pre-, intra-, and postoperative stages.