The energy and economic performance of a transcritical R744 booster supermarket refrigeration system with and without parallel compression and integrated with an organic Rankine cycle (ORC) was investigated. The results obtained were compared with those of a transcritical R744 booster supermarket refrigeration system with and without parallel compression and those of a conventional R404A direct expansion (DX) system. Nine different locations, namely Copenhagen (Denmark), Paris (France), Athens (Greece), New Delhi (India), Phoenix and Miami (US), Madrid (Spain), Bangkok (Thailand) and Riyadh (Saudi Arabia), were considered. It was discovered that the ORC is effective only at ambient temperatures higher than 27 °C when operating without parallel compression and 28 °C when operating with parallel compression. By using the heat recovered from the gas cooler to fuel the ORC, the latter was found to be capable of covering between 4% and 24% of the electricity demand of the R744 system in warm and hot climates (without parallel compression). The simple payback period of the additional investment associated with the ORC was found to be between 1.4 and 2.5 years in warm climate locations, while the same was found to be less than about 0.5 years in locations experiencing hot climatic conditions.