Today, artificial intelligence (AI), as well as making our lives easier, has become an essential component in professional fields, including landscape architecture (LA). It has been integrated into architecture & design software by being developed by data scientists, as well as designers and planners. This development minimizes the time and energy to be spent in the process of comprehensive site analysis. In this study, rather than relying solely on existing architectural software, the aim is to explore the capabilities of ChatGPT as a customizable AI tool for site analysis by integrating domain-specific data and coding inputs. In the near future, by development of these tools by designers and planners, problem detection can be done more clearly, and more qualified designs can be made in a short time. In the process of training AI, Kültürpark in Izmir was chosen as the study area as it has been subjected to various physical and functional changes since the beginning of the 20th century. This research contributes to the development of AI-enabled decision support systems in LA and highlights the importance of human-in-the-loop (HITL) approach, where human intervention validates AI outputs for optimal results.