Natural and man-made disasters at the urban level represent a major challenge to increasing resilience. According to the UN Agenda 2030, Disaster Risk Reduction (DRR) is a priority at the global level. Different actions can be planned and implemented before and after a disastrous event. The focus of this research is on actions to take before the event to increase preparedness. This paper focuses on exercises and training activities designed to reduce the gaps between actions performed before and after disastrous events. These actions include discussion-based and operation-based actions, classified by increasing levels of complexity and capability. Serious Games (SG) represent a discussion-based action with the greatest level of complexity and capability. The objective of this paper is to investigate the potential contribution of SG to increasing preparedness for implementing evacuation procedures and thereby enhancing urban resilience. This implies the knowledge of urban mobility in evacuation conditions. This class of SGs combines Transport Risk Analysis (TRA), Transport System Models (TSMs), and emerging Information and Communication Technology (e-ICT) to reproduce, in a virtual environment, a transport system under evacuation conditions. In this way, it is possible to experiment with evacuation planning procedures in a virtual environment. The principal results of a pilot experiment are presented. The SG framework and its pilot implementation show how the potential contribution to increasing awareness and reducing exposure at the urban level can be quantified. The paper is of interest to urban scientists and public and private decision-makers involved in disaster risk planning processes.