In the context of rapid urbanization, the challenge of accommodating growing populations while enhancing urban desirability has become a paramount concern for city planners worldwide. This study delves into the multifaceted endeavor of understanding urban desirability index, aiming to identify and analyze the attributes that contribute to the allure of large cities. Going beyond traditional perspectives, the research employs association rule mining to uncover hidden interdependencies among urban quality of life attributes that collectively shape citizens’ satisfaction. Furthermore, the study introduces the operative concepts of 'order qualifiers' and 'order winners’, borrowed from the realm of operations management. These concepts provide a novel analytical framework for evaluating pivotal dimensions of urban desirability. Leveraging both survey data and city-level statistical metrics from prominent U.S. urban centers, this research investigates the intricate interplay between economic, social, and environmental facets, thereby illuminating their cumulative influence on the satisfaction of urban residents. Notably, the study identifies median salary and community wellbeing as essential qualifiers shaping urban desirability, while also exploring the impact of nationwide excellence as a determinant of municipal desirability. These discernments serve to empower local governing bodies and policymakers in devising effective strategies for urban development and enhancement.