Transportation as an important component for urban sustainability has been well recognized. Individual and societal well-being are critical indicators of social sustainability. However, little attention, from both a research and policy perspective, has been paid to the impacts of transportation on well-being. With extensive urban expansion resulting from rapid urbanization, commuting has become a physical and mental burden for residents in the megacities of China because of increasing travel distances and worsening travel experiences. This chapter aims to contribute to the growing literature on the relationship between transportation and well-being and also to quantitatively test this relationship by using data from a survey conducted in Xi-an, China. The results from a structural equation modeling analysis suggest that travel characteristics, including travel mode choice and level of service, significantly influence commuting satisfaction, and in turn affect overall satisfaction of life. These findings highlight the importance of transportation-related strategies on improving well-being.