A case study of the Singapore road network provides empirical evi-dence that road pricing can significantly affect commuter trip timing be-haviors. In this paper, we propose a model of trip timing decisions thatreasonably matches the observed commuters’ behaviors. Our model ex-plicitly captures the difference in individuals’ sensitivity to price, traveltime and early or late arrival at destination. New pricing schemes aresuggested to better spread peak travel and reduce traffic congestion. Sim-ulation results based on the proposed model are provided in comparisonwith the real data for the Singapore case study.