The concept of sustainable transportation of goods as the primary paradigm for designing contemporary logistics systems assumes the use of energy-efficient and affordable modes of transport in a way that guarantees the most cost-efficient variant of the delivery scheme. That especially applies to road transport deliveries, where the number of alternatives for organizing the transportation process is numerous and the choice of the optimal solution is complicated by the multiple stochastic influences of the environment on the technological processes. In this paper, we contribute to solving the problem of shaping the sustainable delivery schemes by proposing an approach to shape the complete set of alternative transport and technological schemes for packaged cargo delivery by road transport. The developed mathematical model allows estimating the efficiency of each alternative delivery scheme for the given request and chooses the best variant that minimizes the total costs of all participants in the delivery process. The proposed algorithms are implemented in the C# programming language within the frame of a class library for modeling transport delivery processes. A case of transport processes for Delivery Ltd. (Kharkiv, Ukraine) is applied to illustrate the procedure of using the developed approach to choose the optimal transport and technological schemes for long-distance deliveries. As the result of simulating the goods transportation processes, we show the regression models that represent dependencies of the total costs for the implementation of a delivery scheme from the parameters of demand for the transportation of goods. These regression models allow estimating the most efficient delivery schemes based on the functional analysis of the obtained dependencies for the given demand parameters.