His work spans a number of infrastructure systems with an emphasis on transportation. Using stochastic models to characterize infrastructure component performance and failure, failure trees, and simulations, Chester and his students characterize the performance of infrastructure systems under extreme heat and flooding. Chester is the co-leader of the Urban Resilience to Extremes Sustainability Research Network, a consortium of 10 cities across North and South America working together to develop adaptation strategies for urban infrastructure from extreme events. He maintains a body of research focused on life cycle assessment of transportation systems.