This paper presents results obtained for the vibratory compaction process of road structures, in which the natural soil is used for the foundation infrastructure. The experiments and the optimization of the compaction process were carried out on five road lanes in Transilvania, Romania. A self-propelled single-drum roller compactor, BOMAG BW 213 S-5, was used for the compaction, layer by layer, with six successive passes over each layer. For each layer, the initial degree of compaction was measured, and after the fifth pass, it achieved the value prescribed in the road construction project. After each pass over the same layer, its settlement increased due to the plastic deformation and the soil’s rigidity receiving discrete higher values. This is how five different discrete values for rigidity were obtained. Modeling the compaction process is carried out using the Kelvin–Voigt model, with discrete variable experimental values for soil rigidity and assumed constant viscous damping values. Based on the two-degree-of-freedom linear elastic model, graphs were plotted for vibration amplitude variation and for the force transmitted to the soil when the excitation pulsation varies continuously and the soil rigidity varies discretely. There is a relationship between the initial and final degree of compaction values in the ratio that was proven to be dependent on the ratio of amplitude values corresponding to the final and initial roller passes cycle. The result is a useful relationship for the “in-situ” estimation of the compaction process effect. The novelty of this research is that it demonstrates the change in soil rigidity values after each pass of the vibratory roller and, thus, the increase of its settlement (plastic deformation) and the “slipping” for the amplitude resonance peak by discrete increasing values. Calibration of the resonance vibrations regime in accordance with the degree of compaction determined by geotechnical methods for “in-situ” sample prelevation stands as a fast and efficient method for the evaluation of the final degree of compaction value. This is, implicitly, the method for estimating the number of vibratory roller passes in the road construction project. In conclusion, the novelty of the research consists in the fact that, through using the resonance response of the vibratory roller, a correlation was made with the degree of compaction achieved after each pass