The purpose of this paper is to propose measures for maximum practicable use of information and communication technologies in Ukraine while on cross-border movement of goods and means of transport. For today Ukraine has been intensively implementing the Single Window system, almost completely switched to electronic declaration as well as electronic submission of the documents and information required for official controls of goods belonging to entities or self-employed persons. A passenger declaration, filled out in advance and sent to customs authorities, for goods in accompanied/unaccompanied baggage or freight shipment can also significantly simplify procedures at a border crossing. The effectiveness of the measures proposed is proved using system analysis of well-structured problem by applying critical path method in a PERT diagram and Monte Carlo method for determining optimal time characteristics of handlings. Modeling alternative sequence scenarios of the process of customs clearance at the customs offices of departure and destination allows determining additive components of the total delivery time within customs territory of Ukraine. The scenarios include improvements in Single Window system, establishment of information and communication system for e-declaration of natural persons’ goods and currency valuables. In this regard, first and foremost, experience of different countries on these issues as well as organisational, legal and technical difficulties are analyzed, and then directions for the development are outlined using mini-Delphi approach. In summary, the theoretical relevance of the research lies in the development of the mathematical model for the processes described, practical application of the improvements will reduce delays and additional delivery costs.