Population transfer via chirped rapid adiabatic passage is studied using open quantum and semiclassical models, with and without the rotating-wave approximation. A time-dependent variational approach based on the multiple-Davydov D₂ trial state is employed to simulate the quantum models with an arbitrary finite mean photon number. We examine the accuracy of both the semiclassical field description and the rotating-wave approximation. Robust population transfer is identified over a wide parameter regime controlled by the laser spectral chirp and is found to be insensitive to the spin–phonon coupling strength, Gaussian pulse area, and energy gap of the two-level system.