We theoretically study the dynamical phase diagram of the Dicke model in both classical and quantum limits using large, experimentally relevant system sizes. Our analysis elucidates that the model features dynamical critical points that are distinct from previously investigated excited-state equilibrium transitions. Moreover, our numerical calculations demonstrate that mean-field features of the dynamics remain valid in the exact quantum dynamics, but we also find that in regimes where quantum effects dominate signatures of the dynamical phases and chaos can persist in purely quantum metrics such as entanglement and correlations. Our predictions can be verified in current quantum simulators of the Dicke model including arrays of trapped ions.