Soil investigations concerning cyclic loading focus on the evaluation, in particular, of design parameters, such as elastic modulus, Poisson’s ratio, or resilient modulus. Structures subjected to repeated loading are vulnerable to high deformations, especially when subgrade soils are composed of cohesive, fully-saturated soils. Such subgrade soils in the eastern part of Europe have a glacial genesis and are a mix of sand, silt, and clay fractions. The characteristic of, e.g., Young modulus variation and resilient modulus from repeated loading tests, is presented. Based on performed resonant column and cyclic triaxial tests, an analytical model is proposed. The model takes into consideration actual values of effective stress p′, as well as loading characteristics and the position of the effective stress path. This approach results in better characterization of pavement or industrial foundation systems based on the subgrade soil in undrained conditions. The recoverable strains characterized by the resilient modulus Mr value in the first cycle of loading was between 44 MPa and 59 MPa for confining pressure σ’3 equal to 45 kPa, and between 48 MPa and 78 MPa for σ’3 equal to 90 kPa. During cyclic loading, cohesive soil, at first, degrades. When pore pressure reaches equilibrium, the resilient modulus value starts to increase. The above-described phenomena indicate that, after the plastic deformation caused by excessive load and excess pore water pressure dissipation, the soil becomes resilient.