The duality symmetries of various chiral boson actions are investigated using D=2 and D=6 space-time dimensions as examples. These actions involve the Siegel, Floreanini-Jackiw, Srivastava and Pasti-Sorokin-Tonin formulations. We discover that the Siegel, Floreanini-Jackiw and Pasti-Sorokin-Tonin actions have self-duality with respect to a common anti-dualization of chiral boson fields in D=2 and D56 dimensions, respectively, while the Srivastava action is self-dual with respect to a generalized dualization of chiral boson fields. Moreover, the action of the Floreanini-Jackiw chiral bosons interacting with gauge fields in D=2 dimensions also has self-duality but with respect to a generalized anti-dualization of chiral boson fields.