Unsafe road crossing behavior by pedestrians is a main contributing factor of pedestrian casualties. Data from 2006 to 2012 in Delhi, India, show that pedestrians have the largest share in total road fatalities. Although facilities such as underpasses and overpasses are often provided to help cross a road, most often, pedestrians do not use them. Pedestrian perceptions play an important role in the use of such facilities. This study examined the relationship between actual crash risk and perceived risk for selecting crossing facilities by pedestrians. The road crossing preferences of pedestrians were analyzed for midblocks, intersections, and locations with a flyover where overpasses and underpasses are provided for road crossing. Responses covering safety and convenience of using specific facilities from one thousand pedestrians were collected through a structured questionnaire on selected locations. A path analysis model, i.e., a special case of structural equation modeling, was developed for analyzing the data. Results show that an inverse relationship exists between actual and perceived crash risks. Crossing behavior in midblocks was found to mediate this relationship. At locations with a flyover, the perspective of convenience was significantly related to the actual crash risk. This study identifies the potentially useful roles that pedestrian perceptions of risk and preferences in road crossing can play in avoiding actual crashes involving pedestrians. Pedestrians’ demographics was also analyzed with perceived risks and preferences for road crossing. From a policy standpoint, the relationships identified between actual and perceived risk and the built environment features of road crossing provide useful information for transportation planners, city planners and engineers. Since perceived risk influences travel behavior, it is important to study influence of perceived crash risk for pedestrians. Proactive interventions are required at the locations with low crash rates as the perceived risk by pedestrians is quite high at these places. This is in addition to the measures required at the locations associated with high actual crash risk faced by pedestrians though these locations are having low perceived crash risk. © 2020 Hong Kong Society for Transportation Studies