Chiral macrocyclic arenes possess confined three-dimensional asymmetric cavities, electron-rich structures, chiral luminescence properties and excellent enantioselective recognition properties and have become a frontier and hotspot of macrocyclic chemistry and supramolecular chemistry. In recent years, there has been growing interest in the development of novel chiral macrocyclic arenes, which have found applications in various research areas. In this review, the construction, properties and functional applications of novel chiral macrocyclic arenes in enantioselective recognition, chiral sorting and construction of chiral luminescent materials according to their chiral types, including central, axial, planar, and inherent chiralities, are summarized. It is expected that this review will be helpful for research on supramolecular chemistry and for promoting the development of synthetic chemistry, materials chemistry and biochemistry.