We show that the counter-rotating terms of the dispersive qubit-cavity Rabi model can produce relatively large and nonmonotonic Bloch-Siegert shifts in the cavity frequency as the system is driven through a quantum-to-classical transition. Using a weak microwave probe tone, we demonstrate experimentally this effect by monitoring the resonance frequency of a microwave cavity coupled to a transmon and driven by a microwave field with varying power. In the weakly driven regime (quantum phase), the Bloch-Siegert shift appears as a small constant frequency shift, while for strong drive (classical phase) it presents an oscillatory behaviour as a function of the number of photons in the cavity. The experimental results are in agreement with numerical simulations based on the quasienergy spectrum.The Rabi Hamiltonian -describing a two-level system coupled to a cavity (resonator) mode -is a paradigmatic model in quantum physics. In the rotating-wave approximation (RWA) it leads to the well-known JaynesCummings (JC) model. In the dispersive limit this model predicts the appearance of ac-Stark shifts in the energy levels of both the qubit and the cavity. The inclusion of counter-rotating terms produces an additional displacement of the energy levels. This Bloch-Siegert (BS) shift [1] is usually very small on standard experimental platforms since it depends on the ratio between the coupling and the sum of the Larmor and cavity frequencies. Recently however, significant experimental effort has been put into increasing the coupling to values comparable with the Larmor frequency [2-4], most notable in semiconductor dots [5,6] and superconducting circuits [7][8][9][10][11][12]. Other approaches for observing the Bloch-Siegert shift include the detailed analysis of two-level Landau-Zener spectra of Rydberg atoms [13,14] and Cooper-pair boxes [15][16][17], as well as the simulation of the Rabi model in rotating frames [18,19].In this work we take a different route. We recognize that the counter-rotating terms do not conserve the excitation number. Therefore, the natural framework for their experimental demonstration is that of driven-dissipative systems [20,21]. Guided by this intuition, we realize a setup consisting of a transmon [22] dispersively coupled to a cavity, where the cavity is driven at a fixed off-resonance microwave tone, while at the same time the spectrum is scanned by a comparatively weaker probe field, see Fig. 1. At low driving powers, we observe the expected vacuum ac-Stark shift [23][24][25][26][27]. This is followed by a transition regime dominated by nonlinear effects as the power is increased. For the Jaynes-Cummings model, such transition has been predicted and studied in the resonant qubit-cavity case [28][29][30][31]. In the dispersive limit, the transition region is no longer abrupt, but it is We drive the cavity with a detuned drive frequency ω d < ω c . The spectrum of the system is monitored by a weak probe with frequency ω p , which is swept within the window [4.36, 4.39] GHz. (d) In the T 1 measu...