Pillararenes have columnar architectures with electron-rich cavities to endow themselves with unique host-guest complexation capability. Easy structural modifiability facilitates them to be used in many applications. Currently, pillararene based drug delivery systems (DDSs) have been developed as a powerful tool for precise diagnosis and treatment of cancer. Various functional guest molecules could be integrated with pillararenes to construct nanomaterials for cancer chemotherapy, phototherapy and chemodynamic therapy. In order to improve cancer therapy efficacy, active targeted DDSs have become particularly important. Benefiting from the good host-guest properties and structural variability of pillararenes, tumor targeting groups could be easily introduced into pillararene based DDSs to realize precise drug delivery at tumor sites. In this feature article, we provide a comprehensive summary of the present design strategy for pillararene based active targeted DDSs, which can be classified into three types namely host-guest complexation, charge reversal and targeted group modified pillararenes. Some important examples are selected to for a detailed discussion on their respective strengths and weaknesses.