The aim of the paper is to critically evaluate the similarities and differences in the development of the temporal and spatial structure of shopping centers in the Czech and Slovak republics. We focused on the retail transformation and sustainable manifestations of the location and construction of shopping centers. We classified shopping centers according to their genesis, location in the city, and size of the gross leasable area. To analyze migration trends and geographic distribution characteristics of shopping centers in the capital cities of both countries (local level of analysis), we used spatial gravity and standard deviational ellipse. Generally, there is an analogous trend in the development of shopping centers in the Czech Republic and Slovakia, with a particular two- to four-year lag in Slovakia (west–east gradient). Despite this, we still perceive the demand for shopping centers in both countries as above average, and it is not declining. The construction of shopping centers, mainly in small towns, also indicates this trend. In Prague and Bratislava, the pattern of spatial expansion of shopping centers differs. Prague probably represents a more advanced phase of shopping center agglomeration. However, neither country has reached the state of clustering.