A physical model to examine impact oscillators has been developed and analyzed. The model accounts for the viscoelastic impacts and is capable to mimic the dynamics of a bounded progressive motion (a drift), which is important in practical applications. The system moves forward in stick-slip phases, and its behavior may vary from periodic to chaotic motion. A nonlinear dynamic analysis reveals a complex behavior and that the largest drift is achieved when the responses switch from periodic to chaotic, after a cascade of subcritical bifurcations to period one. Based on this fact, a semianalytical solution is constructed to calculate the progression of the system for periodic regimes and to determine conditions when periodicity is lost.