Pregnant women are at high risk of coronavirus disease 2019 (COVID-19) complications, including acute respiratory distress syndrome (ARDS) and the need for mechanical ventilation. There is no literature on the optimal strategy for the management of difficult-to-wean pregnant and early postpartum patients.We report two cases of pregnant women with COVID-19 pneumonia and ARDS, who required mechanical ventilation and high doses of analgesia, and sedation with neuromuscular blocking agents to facilitate ventilation and oxygenation. Both patients had a tracheostomy procedure to facilitate weaning from mechanical ventilation and sedation. Shortly after tracheostomy, sedation and analgesia, along with ventilatory support were weaned off. Both patients were discharged home. These cases propose early tracheostomy as a strategy to facilitate weaning from mechanical ventilation and sedation in pregnant and early postpartum patients.