To meet the goal of worldwide decarbonization, the transformation process toward clean and green energy structures has accelerated. In this context, coal-fired power plant (CFPPs) and large-scale energy storage represented by compressed air energy storage (CAES) technology, are tasked with increasing renewable resource accommodation and maintaining the power system security. To achieve this, this paper proposes the concept of a CFPP–CAES combined cycle and a trigenerative system based on that. Considering the working conditions of the CFPP, thermal characteristics of three typical operation modes were studied and some general regularities were identified. The results of various potential integration schemes discussion indicated that extracting water from low-temperature points in the feedwater system to cool pressurized air and simultaneously increase the backwater temperature is beneficial for improving performance. In addition, preheating the pressurized air before the air expanders via low-grade water in the feedwater system as much as possible and reducing extracted steam contribute to increasing the efficiency. With the optimal integration scheme, 2.85 tonnes of coal can be saved per cycle and the round-trip efficiency can be increased by 2.24%. Through the cogeneration of heat and power, the system efficiency can reach 77.5%. In addition, the contribution degree of the three compression heat utilization methods to the performance improvement ranked from high to low, is preheating the feedwater before the boiler, supplying heat, and flowing into the CFPP feedwater system. In the cooling energy generation mode, the system efficiency can be increased to over 69%. Regardless of the operation mode, the benefit produced by integration is further enhanced when the CFPP operates at higher operating conditions because the coupling points parameters are changed. In addition, the dynamic payback period can be shortened by 11.33 years and the internal rate of return increases by 5.20% under a typical application scenario. Regarding the effect of different application scenarios in terms of economics, investing in the proposed system is more appropriate in regions with multiple energy demands, especially heating demand. These results demonstrate the technical advantages of the proposed system and provide guiding principles for its design, operation, and project investment.