Aims and background: Prolonged mechanical ventilation is frequently required in severely ill patients. The goal of the study is to describe the outcomes of critically ill patients who are mechanically ventilated for >14 days and the effect of late tracheostomy vs late extubation on their outcome. Patients and methods: A retrospective descriptive study was conducted at a single intensive care unit (ICU) at an academic tertiary medical center. All patients were admitted to the ICU on mechanical ventilation for >14 days over a 5-year period (1st January 2016–31st December 2020). The main outcome measures analyzed were length of ICU stay and inhospital mortality. Results: A total of 179 patients were hospitalized in the ICU for >14 days. Of these, 36 were mechanically ventilated for greater than 14 days, 26 of them eventually underwent a tracheostomy, and 10 were extubated. As compared to the extubated patients, the cohort receiving the tracheostomy all had significantly longer ICU lengths of stay (27 vs 47.5 days, p-value 0.0017), length of hospitalization (29.5 vs 52 days, p-value < 0.05), and total days of mechanical ventilation (21.5 vs 46 days, p-value < 0.05). There was no significant difference between the days of endotracheal (ET) intubation, ventilator-associated pneumonia (VAP), albumin (Alb) and hemoglobin (Hb) levels, ICU death, or discharge. Undergoing tracheostomy resulted in a longer ICU/hospitalization without a change in overall inhospital mortality. Conclusion: Performing late tracheostomy after 14 days may prolong hospitalization without improving inhospital survival. Clinical significance: All efforts should be made to determine the need for, and subsequently perform, a tracheostomy. For whatever reasons, this is delayed beyond 14 days, the team should reevaluate the benefit to the patient and potential for possible ET extubation from mechanical ventilation.