Transportation is a key logistic function, which determines the dynamic nature of material flows in logistic systems. At the same time, transportation is a source of uncertainty of logistics operations performance in the supply chain. Obviously, the development of a new approach for evaluation of the duration of delivery just in time will improve the efficiency of supply chains in accordance with one of the major criteria, namely customer satisfaction. The paper is devoted to the formation of analytical and simulation models, which allow obtaining the probabilistic evaluation of the implementation of unimodal and multimodal international transportation “just in time”; the developed algorithm takes into account main indices of transportation and various constraints (technical, organizational, administrative); performed calculation examples prove the legitimacy of the developed approach.