This paper presents a practical approach for collecting cargo from multiple points by changing the aircraft’s heading angle. This approach aims to find the shortest retrieval distance through simulation analysis. The Traveling Salesman Problem (TSP) optimization technique is used to calculate the retrieval distance. In the simulation analysis, this paper establishes a dynamic model for the airdrop process and introduces a calculation method for determining the airdrop release point. Moreover, it analyzes the uncertainties in the parameters of the parachute-body system and considers the characteristics of the TSP problem. The simulation results show that accounting for the heading angle can effectively reduce the retrieval distance and improve the collection efficiency. This research significantly advances the development of technology for collecting multi-point airdropped cargo.