This chapter aims to contribute to the body of knowledge in geography teaching on the nature of and challenges to developing geographical thinking in Chilean schools. The discussion that follows first identifies the kinds of geography subject knowledge taught in Chile and second identifies the pivotal role of the way in which teachers perceive and develop their own geographical thinking and how this translates into their classroom practice. We performed lesson observations and interviews with forty-nine geography teachers in Chile across two networks: Teachers of Teachers and Rural Micro Centres. Findings, show that there is a strong tension between teacher training, and teachers’ own learning as in-service teachers. The paper concludes that developing geographical thinking in Chilean schools is influenced by a complex range of inter-related factors including the quality of teacher geography knowledge, their different interpretations of geography knowledge and their application of these in classroom practices.