Resilience can have desirable and undesirable consequences. Thus, resilience should not be viewed as a normative desirable goal, but as a descriptor of complex systems dynamics. From this perspective, we apply resilience thinking concepts to assess the dynamics of inequality, spatial segregation, and sustainability in Chile’s capital city of Santiago. Chile’s economy boosted since democracy was restored in 1990, but continuity of neoliberal reforms and transformations of Pinochet’s dictatorship (1973–1990) seem to have locked Chilean cities in resilient, albeit unsustainable, patterns of uneven development. Socio-economic data from Santiago shows highly resilient patterns of urban inequality and segregation from 1992 to 2009 despite democratic efforts, political agendas and discourses packed with calls for reducing poverty and inequality. We present a conceptual model based on the notion of stability landscapes to explore potential trade-offs between resilience and sustainable development. We mapped Santiago’s spatio-temporal inequality trends and explored if these patterns support an inequality-resilience stability landscape. Analysis of temporal and spatial distribution of development assets across four human development dimensions (i.e., income, education, health, democracy) revealed potential socio-political and spatial feedbacks supporting the resilience of inequality and segregation in Santiago. We argue that urban sustainability may require breaking this resilience, a process where bottom-up stressors such as social movements could play a key role.