The reason for changes in ranking within urban systems is the subject of much debate. Employing the census data from 1990 to 2020, this paper investigates population dynamics across urban hierarchies and its influencing factors in the Yangtze River Delta. The results reveal an upward pattern of population dynamics and show that the advantages of high-ranking cities in population gathering are obvious, though they have declined recently. Based on a framework of urban amenity and the ridge regression model, the authors argue that concerns of residents in choosing cities in which to settle are gradually changing from economic opportunities to multidimensional amenities, finding that the influencing mechanisms vary across time. This is slightly different from Glaeser’s consumer cities; economic gains, as physiological needs, are always important for population growth. As higher-level needs, social and natural amenities, including Internet accessibility and urban green space, did not affect growth until the turn of the new millennium. In terms of negative factors, the ‘crowding-out effect’ of living costs and environmental pollution are not significant, as theoretically expected, suggesting that residents tend to care more about development opportunities than the negative impacts of living in high-ranking cities. Finally, policies are proposed to promote population growth and the coordinated development of large, medium, and small cities in the Yangtze River Delta.