The integration of intelligent decision-making algorithms with urban cultural expression is becoming a hot topic in both academic and practical fields for exploring urban street landscapes. Exploring the application strategies of intelligent decision-making algorithms and regional cultural expression in street landscape pattern recognition and innovative design is a key step. The single layout of urban street construction, cultural deficiency, ecological imbalance, and low resident participation seriously constrain the overall quality improvement of the city. To address this dilemma, this study delved into Kunming City and selected the ten “most beautiful streets”, such as Dianchi Road, for research. By using the Analytic Hierarchy Process, a comprehensive evaluation system covering multiple dimensions, such as the street layout, plant landscape, and historical culture, was constructed to analyze the street landscape of Kunming. The research results indicate that the top four roads in terms of weight evaluation scores are Cuihu Ring Road, Jiaochang Middle Road, Qingnian Road, and Beijing Road, with values of 0.2076, 0.1531, 0.1274, and 0.1173. The weight reveals that each street has its unique landscape factors, such as the profound cultural heritage of Cuihu Ring Road and the beautiful plant landscape of Jiaochang Middle Road. Further analysis also reveals the close relationship between various factors in the evaluation model, emphasizing the importance of supplementing material and cultural elements in street landscape design. The significance of this study goes beyond a single analysis of the street landscape in Kunming City. Drawing a regional street landscape pattern map sets an example for other cities to build distinctive, eco-friendly, culturally rich, and highly humanized street spaces, providing reference and inspiration. More importantly, this study promotes the application and development of intelligent decision-making algorithms in the field of urban landscapes. Future research will further optimize algorithms to improve their adaptability and accuracy in complex environments.