Canada and the United States are heavily dependent on a few border crossing locations to facilitate international trade between the two countries. These crossings cost firms extra time and uncertainty in their supply chains that reduce the effectiveness of trade. Therefore, a great need exists to study the movement of vehicles traversing these border locations and identify characteristics that make these locations attractive. To this end, this study utilizes GPS data to study trucks traveling between the transportation hubs in Toronto, Ontario, Canada, and Chicago, Illinois. Two feasible choices are available for these trucks to cross the international border: Blue Water Bridge and Ambassador Bridge. Although most route choice decisions are based primarily on reducing travel time, a unique aspect of this corridor is that the total trip time by route is relatively even. A logit model was estimated to identify other factors that may influence the route choice decisions of trucks in the Toronto–Chicago corridor. The results suggest that a higher average crossing delay for a given time of the day has a negative influence on the selection of a given border crossing. Such an effect is more pronounced for the Blue Water Bridge. Other factors influencing the choice of crossing include the type of industry served by the truck, the carriers operating the trucks, time of the day, and day of the week.