Uncertainty is an essential factor in transportation. For example, one cannot predict exactly the travel time from home to work. Conventional transportation pedagogy is mainly focused on modeling deterministic situations because of the complex mathematics required for modeling uncertainty. We develop a framework for effectively teaching uncertainty modeling in transportation using the example of travel time uncertainty. The objective is for students to appreciate the significance of incorporating uncertainty in planning without resorting to lengthy and intimidating mathematics. The framework that is developed contains strategies for introducing travel time uncertainty, method for appreciating the impact of the uncertainty, approaches of modeling the uncertainty in planning problems, projects for students to practice, and assessment tasks.