Flexible Carpooling is the use of an innovative set of technologies that supports the formation of ‘on-the-spot’ carpools, in an effort to better utilize existing road capacity. Transportation Analytics contributed to a preliminary feasibility study that addresses the key implications of implementing such a system in the United States. Using a case-study approach focused on five congested corridors in the San Francisco Bay Area, we developed a generalized cost model based on a data analysis of the key local drivers of transportation mode choice. The model shows how existing and potential commuters would be impacted by alternative system deployment options, as well as major market forces and selected commuter characteristics. The combined scenarios illustrate how different implementations of flexible carpooling result in varied impacts to the five case study corridors.