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The evolution of an urban settlement system in the post-Soviet space is analyzed by the comparison of the progress of urbanization and changes in migration balances of cities of different size, status, and location in Russia, Ukraine, and Belarus. Despite the differences in size and density of cities, their hierarchical and spatial structure, and management decisions, many trends in the development of city systems were similar in these countries. The reasons for different migration attractiveness of cities of different sizes are discussed including their socioeconomic statuses and infrastructural arrangement. These countries are characterized by strong contrasts in urban settlement patterns where large and very large centers play a major role and there is a significant proportion of small towns. In all three countries, there are significant differences between the quality of life in large urban centers and small towns. The situation before the military events in Ukraine in 2014 is analyzed. Migration in the period of 1990–2013 mostly from rural areas and from small and medium-sized cities to major centers supports the hypothesis of renewed urbanization that had gone uncompleted in Russia, Ukraine, and Belarus in the Soviet era. Two main migration directions can be noted in the post-Soviet period: from rural areas to capitals, their suburbs, and other large cities, and for Russia and Ukraine (until 2014), from the east to the central and southern regions.