We analyse the Chilean Spring of 2019-2020 - the fiercest social outburst in Chile during the last three decades. After discussing the combined role of long-standing grievances, political attitudes, and cultural change in triggering the outburst, we study the interplay among peaceful and violent protests and criminal activity. We argue that brutal police repression and governmental mismanagement contributed to deepening the crisis once it exploded. We conclude by describing the attempts of the political class to cope with the crisis and speculate about its potential political consequences, especially for the Chilean party system.