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Cities have a unique place in the history and philosophy of democracy. Yet there is little quantitative empirical research investigating the extent to which urbanization makes an independent contribution to political change. Does the growth of cities in a country increase the likelihood of democratization? This question is important in contexts of urbanization without industrialization in many low- and middle-income countries today. We address this gap with a novel empirical strategy combining (a) cross-national regressions analyzing the determinants of levels of democracy and episodes of regime transition since 1960 in 161 countries, with (b) analysis of self-reported political attitudes and actions of over 160,000 individuals across a range of city sizes from 59 countries. We conclude that city living has little independent effect on individual preferences for democracy, but it does facilitate political participation. At the macro scale, urban population growth is associated with an increased likelihood of political transition.