Understanding factors that drive the parking choice of commercial vehicles at delivery stops in cities can enhance logistics operations and the management of freight parking infrastructure, mitigate illegal parking, and ultimately reduce traffic congestion. In this paper, we focus on this decision-making process at large urban freight traffic generators, such as retail malls and transit terminals, that attract a large share of urban commercial vehicle traffic. Existing literature on parking behavior modeling has focused on passenger vehicles. This paper presents a discrete choice model for commercial vehicle parking choice in urban areas. The model parameters were estimated by using detailed, real-world data on commercial vehicle parking choices collected in two commercial urban areas in Singapore. The model analyzes the effect of several variables on the parking behavior of commercial vehicle drivers, including the presence of congestion and queueing, attitudes toward illegal parking, and pricing (parking fees). The model was validated against real data and applied within a discrete-event simulation to test the economic and environmental impacts of several parking measures, including pricing strategies and parking enforcement.