With the acceleration of urbanization, waterlogging has become an increasingly serious issue. Road waterlogging has a great influence on residents’ travel and traffic safety. Thus, evaluation of residents’ travel difficulties caused by rainstorm waterlogging disasters is of great significance for their travel safety and emergency shelter needs. This study investigated urban rainstorm waterlogging disasters, evaluating the impact of the evolution of such disasters’ evolution on residents’ evacuation, using Daoli District (Harbin, China) as the research demonstration area to perform empirical research using a combination of scenario simulations, questionnaires, GIS spatial technology analysis and a hydrodynamics method to establish an urban rainstorm waterlogging numerical simulation model. The results show that under the conditions of a 10-year frequency rainstorm, there are three street sections in the study area with a high difficulty index, five street sections with medium difficulty index and the index is low at other districts, while under the conditions of a 50-year frequency rainstorm, there are five street sections with a high difficulty index, nine street sections with a medium difficulty index and the other districts all have a low index. These research results can help set the foundation for further small-scale urban rainstorm waterlogging disaster scenario simulations and emergency shelter planning as well as forecasting and warning, and provide a brand-new thought and research method for research on residents’ safe travel.