Chile is known as a country that has applied the neoliberal recipes of the Chicago School to the extreme. Within this context, Chilean trade union law is extraordinarily restrictive and regulatory. Neoliberal legislation has limited the right to strike, disfiguring it when compared to the doctrine of the ILO’s committee on freedom of association. In this work, we will refer to two observable trends within this context: one purely legal and the other factual. The legal trend refers to how academics and the courts have interpreted Pinochet’s 1980 constitution broadly and evolutionarily to admit the strike as a constitutional right. On the other hand, unions and workers increasingly resort to strikes outside the legal framework, and with atypical modalities. Both trends intersect when the courts have upheld atypical strikes as a constitutional right for workers. However, both directions have not been sufficient to develop strengthened unionism in Chilean labour law.