Chirality and luminescence are important for both chemistry and biology, which are highly influenced by aggregation. In this work, we reported a pair of metalated tetraphenylethylene(TPE)-based organic cage enantiomers, which feature a quadrangular prismatic cage structure. These homochiral cages exhibit concentration-dependent chiral behaviors alongside a propensity for thermodynamic aggregation. Aggregation caused quench effect is found for these cages accompanying the increasing of the concentrations. When a poor solvent is added to produce a kinetical aggregation, the aggregation-annihilation circular dichroism and aggregation-induced emission behaviours are observed for these enantiomeric cages. By comparing these observations with the photophysical behaviors of a pair of structurally similar organic molecular enantiomers, the unique photophysical properties observed are intricately linked to the metal-integrated TPE-functionalized cage structures.