This article examines the background in which enterprises called free schools, as well as complementary educational activities, have taken root in Chile. Two kinds of recently burgeoning free schools are identified; one supplementing regular schooling with a social justice focus, and another that is a fully fledged alternative to other schooling. The history of freedom itself in Chile is explored from a historical perspective, contrasting somewhat with freedom as it is understood in more developed countries. Parallels to Anglophone free schools such as AS Neill's Summerhill are also discussed, as well as the sociopolitical context in which Chilean free schools continue to develop.