With deepening cooperation between China and ASEAN countries, the driving force of Chinese enterprises’ location choice for direct investment in ASEAN should not only consider their own competitive advantages but also consider environmental and resource factors such as geography, economy and culture of the host country. Therefore, this paper first expounds on the location choice of Chinese enterprises’ investment in ASEAN and then presents research hypotheses based on the enterprises’ own experiences and the three proximities of geography, economy and social culture. A Probit regression analysis model is adopted to analyze the evolutionary driving force of Chinese enterprises’ investment locations in ASEAN. The study reveals the following findings: First, Chinese enterprises’ investments in ASEAN countries exhibit a “clustering-dispersal” pattern in industries such as energy, transportation and real estate forming industrial clusters of various ASEAN cities. Second, the attributes of multinational corporations, including corporate characteristics, geographical factors, economic factors, and cultural factors, significantly influence the expansion of the ASEAN investment network, and heterogeneous investment preferences exist across different regions.