Energy saving and emission reduction of engines were taken seriously, especially for vehicular diesel engines. Exhaust heat recovery based on organic Rankine cycle (ORC) system has been considered as an effective approach for improving engine fuel economy. This article presents the investigation of water or air cooling method for an ORC exhaust heat recovery system on a heavy-duty truck through simulations. The models of the truck engine and the ORC system were developed in GT suite, and the integration system model was developed in the Simulink environment. The validity of the models was verified experimentally. The performance of the vehicular engine with ORC system using water or air cooling method was comparatively analyzed. The simulation results indicated that the water cooling method is more suitable for the vehicular ORC system than air cooling method. The relation between benefit and penalty of the ORC system and cooling system was discussed. The operating condition of the cooling system was confirmed having significant effects on the combined system performance, especially the fan speed. The performance improvement of the engine with the use of ORC system was further evaluated under different engine operating conditions and ambient temperatures. Lower ambient temperature had positive effects on the engine fuel economy. The mass flow rate of exhaust gas for heat recovery should be regulated for better performance under high ambient temperature.