Stable luminescent π-radicals with doublet emission have attracted growing attention for functional molecular materials. However, their chiroptical properties, particularly their doublet emission-based circularly polarized luminescence, have never been investigated. Here, we investigate the circularly polarized luminescence (CPL) properties of a series of achiral luminescent open-shell π-radicals through various chirality regulation approaches, including induction by a magnetic field, supramolecular coassembly and chiral liquid crystal encapsulation.