Pillar[n]arene is a novel kind of synthetic supramolecular macrocyclic host characterized by its particular pillar-shaped structure consisting of an electron-rich cavity and two finely adjustable rims. Benefiting from its rigid structure, facile synthesis, ease of functionalization, and outstanding host-guest chemistry, pillar[n]arene shows great potential for diverse applications. Significantly, the host-guest recognition of pillar[n]arene provides a novel approach for chemosensing and imaging. Herein, this Review critically and comprehensively reviews the applications of pillar[n]arene-based host-guest recognition in chemosensing and imaging. The sensing and imaging mechanisms as well as the unique roles and advantages of pillar[n]arene-based host-guest recognition are summarized. In addition, preparations of hybrid materials based on pillar[n]arene and inorganic materials are also introduced comprehensively in the light of chemosensing and imaging. Finally, current challenges and perspectives on pillar[n]arene-based host-guest recognition in chemosensing and imaging are outlined.