This paper investigates the differences in the environmental and economic impacts of applying a prospective free-flow Open Road Tolling (ORT) system in Greece, compared with conventional tolling focusing on Road Freight Transport (RFT). The sector of RFT highlights the negative impact of frequent stops for toll payment: increased travel time, reduced road safety, high traffic accident risk, fuel consumption, air pollutant emissions, etc. This research includes a comprehensive international comparison of relevant systems, providing a global perspective on tolling practices. The environmental and economic impacts on a local scale are estimated, and, in addition, there is a rough estimation of the annual cost of fuel consumption of RFT due to the non-application of ORT in Greece, aiming to highlight the need for implementation of ORT in Greece. Only using RFT fuel consumption cost during the year 2017, while the diesel cost was much lower than today, and the same goes for the number of toll stations in Greek motorways, it was found that each year 15 million euros more are spent due to the absence of free-flow ORT in Greek motorways. This amount probably has already tripled.