In this work, site-selective C–H activation at C-5, C-3 and C-2 positions of chromones for the introduction of structural diversity to the chromone scaffold was studied. The keto group of the chromone moiety acts as the directing group for the selective functionalization of chromones at the C-5 position. Furthermore, the C–H functionalization at the electron-rich C-3 position of the chromone can be achieved using electrophilic coupling partners. The C–H functionalization at the C-2 position can be possible using nucleophilic coupling partners. The direct functionalization methods provide a better pathway for the generation of C-5, C-3 and C-2-substituted chromones with good atom economy than that of classical pre-functionalized reaction protocols.