The goal of this study is to evaluate annual and seasonal inflow from the Volga catchment area to the Caspian Sea during the Last Glacial Maximum (LGM ~21,000 years ago) using paleoclimate modeling data. The first approach is based on the LGM simulation by the general circulation models (GCMs) in the framework of the Paleoclimate Modelling Intercomparison Project (PMIP4) and the Coupled Modelling Intercomparison Project (CMIP6). We used four GCMs: INM-CM4-8, MIROC-ES2L, AWI-ESM1-1-LR, and MPI-ESM1-2-LR. The second approach is based on the spatially distributed process-based runoff generation model using PMIP4-CMIP6 model data as boundary conditions. The use of the hydrological ECOMAG model allows us to refine estimates of the Volga runoff in comparison to GCM calculations by considering seasonal features of runoff generation related to periglacial vegetation distribution, permafrost, and streamflow transformation along the channel network. The LGM is characterized by a high uncertainty in meteorological values calculated for the Volga basin using various GCMs. The share of runoff from the three most flooded months from the annual calculated in the LGM was 95%, according to INM-CM4-8, while other GCMs ranged from 69–78%. Three GCMs (MIROC-ES2L, AWI-ESM1-1-LR, and MPI-ESM1-2-LR) showed 83–88% of the present-day value of precipitation in the Volga basin during cooling for more than 10 °C, while INM-CM4-8 showed a two-fold decrease. According to hydrological modeling results using data from three models, the annual Volga runoff was significantly higher than the present-day value, and, when using data from INM-CM4-8, it was lower.