Chiral chemistry is often regarded as the science of studying the stereostructure and symmetry of organic molecules. It mainly focuses on the presence of chiral centers in specific structures and their impact on conformation, properties, and functions. In this field, researchers explore the special properties and potential applications of chiral compounds through synthesis, separation, and characterization. Here, we aim to provide a detailed overview of diverse functionalized cages based on chiral skeletons and their applications in enantioselective recognition and separation, and a diversity of chiral caged skeletons bearing customized functionalities conducted on the recognition and separation of chiral guests.