This paper presents an investigation into the preference structure of commuting mode choice in dense urban areas. The paper aims to investigate the phenomenon of myopic choice and extends the phenomenon to the concept of modal culture. Using a household travel diary survey from the greater Toronto and Hamilton Area, an empirical discrete choice model was estimated. This model was used to provide general comments on the commuting and dependent behaviour of the sample, with a particular focus on the factors that influence bicycling captivation and culture. The model was then used for a hypothetical policy scenario analysis, which found that an investment in biking infrastructure had the capacity to increase bicycling mode share by nearly 50%. Based on this result, this paper recommends further investigation into both data collection for more comprehensive empirical model development and investigation into the policy applicability of the proposed model structure.