In situ shale or kerogen oil production is a promising approach to developing vast oil shale resources and increasing world energy demand. In this study, cyclic subcritical water injection in oil shale was investigated in laboratory conditions as a method for in situ oil shale retorting. Fifteen non-extracted oil shale samples from Bazhenov Formation in Russia (98 °C and 23.5 MPa reservoir conditions) were hydrothermally treated at 350 °C and in a 25 MPa semi-open system during 50 h in the cyclic regime. The influence of the artificial maturation on geochemical parameters, elastic and microstructural properties was studied. Rock-Eval pyrolysis of non-extracted and extracted oil shale samples before and after hydrothermal exposure and SARA analysis were employed to analyze bitumen and kerogen transformation to mobile hydrocarbons and immobile char. X-ray computed microtomography (XMT) was performed to characterize the microstructural properties of pore space. The results demonstrated significant porosity, specific pore surface area increase, and the appearance of microfractures in organic-rich layers. Acoustic measurements were carried out to estimate the alteration of elastic properties due to hydrothermal treatment. Both Young’s modulus and Poisson’s ratio decreased due to kerogen transformation to heavy oil and bitumen, which remain trapped before further oil and gas generation, and expulsion occurs. Ultimately, a developed kinetic model was applied to match kerogen and bitumen transformation with liquid and gas hydrocarbons production. The nonlinear least-squares optimization problem was solved during the integration of the system of differential equations to match produced hydrocarbons with pyrolysis derived kerogen and bitumen decomposition.