Here, we report the experimental observation of a dynamical quantum phase transition in a strongly interacting open photonic system. The system studied, comprising a Jaynes-Cummings dimer realized on a superconducting circuit platform, exhibits a dissipation-driven localization transition. Signatures of the transition in the homodyne signal and photon number reveal this transition to be from a regime of classical oscillations into a macroscopically self-trapped state manifesting revivals, a fundamentally quantum phenomenon. This experiment also demonstrates a small-scale realization of a new class of quantum simulator, whose well-controlled coherent and dissipative dynamics is suited to the study of quantum many-body phenomena out of equilibrium.