A heating, ventilation, or air conditioning (HVAC) system for a building includes an air handling unit (AHU) and a controller. The AHU is configured to provide mechanical cooling for a cooling load in the building when operating in a mechanical cooling state and provide free cooling for the cooling load in the building when operating in a free cooling state. The controller is configured to calculate a minimum free cooling time based on an estimated cost savings resulting from operating in the free cooling state relative to operating in the mechanical cooling state and transition the AHU from operating in the mechanical cooling state to operating in the free cooling state in response to predicting that outside air temperature will be less than a free cooling temperature threshold for at least the minimum free cooling time.