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This article introduces the concept of “counterweight cities” to describe towns that are able to generate an endogenous development process and promote decentralization in traditionally centralist states. This role is accompanied by the prevalence of federalist or autonomist thinking, supported in a local political organization able to inspire changes in the relationships between the different regions within the country. The political group that leads the process is also able to recruit backing in nearby areas. These initiatives have succeeded in consolidating their cities as alternate development poles, displaying dynamic economic and demographic growth, achieving expansion of a modern infrastructure, advanced human resources and cutting- edge cultural and academic assets. Guayaquil in Ecuador and Santa Cruz de la Sierra in Bolivia have benefited from strong ties between the public and the private sector, the presence of a robust locally-based political party and solid inter-regional alliances. These strengths have helped both cities achieve a higher degree of regional autonomy than Concepcion in Chile. The later, has-instead- concentrated in developing as an academic and cultural hub. The cities studied here, enhanced the complexity of the human settlement system in their countries, mitigating the macro cephalic tendencies inherent in the Latin American centralist urban structure. In-depth interviews performed in the three countries allow for a better understanding of the context in which the struggle against centralism took place and was able to overcome the challenges it encountered, in the process of generating substantial counterweights against metropolitan macro cephalism.