Recently, Japan has been hit by more frequent and severe rainstorms and floods. Typhoon Hagibis caused heavy flooding in many river basins in central and eastern Japan from 12–13 October 2019, resulting in loss of life, substantial damage, and many flood insurance claims. Considering that obtaining accurate assessments of flood situations remains a significant challenge, this study used a geographic information system (GIS)-based analytical hierarchy process (AHP) approach to develop flood susceptibility maps for the Abukuma, Naka, and Natsui River Basins during the Typhoon Hagibis event. The maps were based on population density, building density, land-use profile, distance from the river, slope, and flood inundation. A novel approach was also employed to simulate the flood inundation profiles of the river basins. In addition, a crosscheck evaluated the relationship between flood insurance claims and the developed flood risk zones within the river basins. Over 70% of insurance claims were concentrated in high to very high risk zones identified by the flood susceptibility maps. These findings demonstrate the effectiveness of this type of assessment in identifying areas that are particularly vulnerable to flood damage, which can be a useful reference for flood disaster management and related stakeholder concerns for future extreme flood events.