The problems of developing online decision support systems concern the complexity of the transportation management processes, the multi-dimensionality of data warehouses (DWs), and the multi-criteria of decision making. Such issues arise in the management processes by supporting them with adaptable information and communication infrastructure for the management of the freight’s transportation processes. Our research domain involves the assurance of infrastructure for the provision of smart services for the operative management of multi-modal transportation of freights under the conditions of the heterogeneity of communication channels and multi-criteria decision support. The complexity of managing multi-modal transportation processes raises some problems for ensuring the infrastructure for finding more optimal management solutions by the requirements of green development. This research aims to develop the approach for providing the infrastructure of intelligent smart services for adaptable implementation in management processes of online multi-modal freight transportation. The objectives are forwarded to construct the multi-criteria decision-making components and integrate them into the multi-layered, computer-based information management of intelligent systems. We present the steps of extension of the structure of the knowledge-based system with a multi-criteria decision support method, and the possibilities to work under the conditions of wireless networks and the recognition of context-aware situations. The results are demonstrated for the analysis of alternatives by assessing the multi-modal transportation corridors between the East and West regions of Europe, and the opportunities to evaluate them for more effective managerial perspectives under sustainable development requirements.