The chilling effect on freedom of expression is a significant concern across legal systems, discouraging individuals from exercising their right to seek, receive, and impart information. While this effect varies across cultural and legal contexts, international human rights systems provide a framework for understanding and addressing it. This chapter offers a comparative analysis of case law from three major regional human rights courts—the European Court of Human Rights, the Inter-American Court of Human Rights, and the African Court and African Commission on Human and Peoples’ Rights. Selected decisions from the Community Court of Justice of the Economic Community of West African States and the East African Court of Justice are also discussed. This chapter identifies commonalities and regional variations in courts’ approaches to the chilling effect by examining landmark decisions and key principles. It explores how each court defines and conceptualises the phenomenon, the types of state actions or laws recognised as having a chilling effect, the standards of proof applied, and the remedies and reparations granted. This analysis enhances understanding of global standards, highlighting best practices and areas for legal development. It is particularly relevant to legal scholars, practitioners, and advocates working to protect freedom of expression worldwide.