Urban sprawl in South America has for many decades been driven by the housing debate, with major impact on overall urban development. The impact of uncontrolled expansion has been social, economic and environmental degradation to high rates of poverty, poor services and transport. The presence of undeveloped areas within suburban landscapes, such as former infrastructural facilities, obsolete airports, and abandoned train stations, contribute to the impetus to reclaimed and revamped land. These spaces also trigger political aspirations for implementing better practices on “smart” growth, sustainable development and urban regeneration principles. A case in point is the former airport ‘Aeropuerto Cerrillos’ in Santiago, Chile, which closed in 2001 after years of decay; it intended to replace and host a large-scale urban project called ‘Ciudad Parque Bicentenario’. This development is still incomplete and describes a series of pressures on a planning system traditionally adjusted to promote expansion confirming that urban sprawl is still an open agenda triggered by the presence of diverse unexpected urban gaps.