The decision-making process of customers choosing a product or service is complex and dependent on many factors. These factors do not remain unchanged, and customers may change their behavior over time. This is important in markets with alternative products or services, and manufacturers and service providers should effectively monitor customers’ behavior and preferences so that they could be successful in the market. In the freight transportation industry, customers can choose between freight transportation modes. This study sought to identify factors influencing customers’ choices of transportation modes and contribute to transportation managers. Influential factors, e.g., time, safety, and distance, were extracted from the literature. The insignificant factors were excluded through expert views based on the Delphi method, prioritizing the remaining factors through the decision-making and trial evaluation laboratory (DEMATEL)-based analytic network process (DANP) and constructing the DEMATEL matrix of the criteria. It was found that cost, time, speed, safety, and health are the most important determinants of freight customers’ choices of land transportation modes.