The classical chaotic dynamics of the Rydberg hydrogen atom in a semi-infinite dielectric medium is presented. The structure and evolution of the phase space as a function of the scaled energy is extensively explored by means of the Poincaré surfaces of section. The results suggest that for a given dielectric medium the whole phase space structure is regular if the scaled energy is less than the critical energy ε(subscript s). However, if the energy is larger than ε(subscript s), chaos appears. The comparison of our work with the case of a Rydberg atom in a magnetic field suggests that the dielectric dividing surface can play the role of the magnetic field, which is responsible for generating chaos. This study provides a new method for exploring the chaotic dynamical behavior of the Rydberg atom interacting with a dielectric medium.