Background: Even though minimally invasive esophagectomy is a safe and oncologically effective procedure, several authors have reported an increased risk of postoperative hiatal hernia (PHH). This study evaluates the incidence and risk factors of PHH after hybrid minimally invasive (HMIE) versus open esophagectomy (OE). Methods: A retrospective single-center analysis was performed on patients who underwent Ivor Lewis esophagectomy between January 2009 and April 2018. Computed tomography scans and patient files were reviewed to identify the PHH. Results: 306 patients were included (152 HMIE; 154 OE). Of these, 23 patients (8%) developed PHH. Most patients (13/23, 57%) were asymptomatic at the time of diagnosis and only 4 patients (17%) presented in an emergency setting with incarceration. The rate of PHH was significantly higher after HMIE compared to OE (13.8% vs. 1.3%, p < 0.001). No other risk factors for the development of PHH were identified in uni- or multi-variate analysis. Surgical repair of PHH was performed in 19/23 patients (83%). The recurrence rate of PHH after surgical repair was 32% (6/19 patients). Conclusions: The development of PHH is a relevant complication after hybrid minimally invasive esophagectomy. Although most patients are asymptomatic, surgical repair is recommended to avoid incarceration with potentially fatal outcomes. Innovative techniques for the prevention and repair of PHH are urgently needed.