With the advancement of the urban renewal process, the traditional districts in Chongqing have gradually experienced different degrees of transformation, and there currently needs to be more quantitative evaluation and fine control of the current renewal status. As traditional districts’ most important public spaces, streets, and alleys are essential entry points for measuring spatial quality. In this study, 149 sample points in traditional districts of Chongqing were selected. The street spatial quality measurement method was used to quantify the objective spatial characteristics and subjective perception evaluation based on streetscape images, and the two were statistically analyzed. It is found that the sense of enclosure is better created in the traditional districts of Chongqing; the renewal and renovation can substantially improve transparency, tidiness, and imageability. The objective spatial factors that significantly influence the subjective perception evaluation are visible green index, sky view factor, interface density, aspect ratio, visible green index, sky view factor, enclosure, traditional landscape buildings, native trees, cultural relics and historical buildings, color saturation, color brightness, number of businesses, and renovation intensity. This study aims to optimize the spatial quality of streets and alleys by improving subjective perception by optimizing objective spatial characteristics.