Based on the authors’ parallel projects of research and fieldwork in urban informal settlements in Durban and Nairobi, the article uses comparison to bring out similarities and differences in the dynamics of informality in a South African and Kenyan setting. The article examines three dimensions of informality – the informal economy, informal housing and informal politics – as they play into the lives of youth, popular culture, moral debate, and local political contestations. The two historical trajectories of settler colonial statebuilding and urban influx control and segregation in South Africa and Kenya are contrasted, together with the struggles that accompanied decolonisation and the transitions to democracy. The article discusses the ways in which informal entrepreneurship has different weight and possibilities in the South African and the Kenyan case, and shows the impact of different expectations of state delivery in the two environments. In conclusion, the authors try to assess comparatively whether developments in the two cases of urban informal settlement in Durban and Nairobi are converging, or whether they exhibit different patterns of urban integration.