An intense tropical cyclone, Typhoon Jebi, landed the central part of Japan in September 2018 and caused severe damages due to strong winds. Typhoon Jebi obtained the lifetime minimum central pressure of 915 hPa and took a track very similar to past disastrous typhoons: Typhoon Nancy (1961) and Muroto Typhoon (1934). In Osaka City, the 1st, 2nd, and 3rd highest record of instantaneous wind speeds are 60.0 m/s in September 1934, 50.6 m/s in September 1961, and 47.4 m/s in September 2018, respectively, suggesting that a typhoon has been the most threatening windstorm in the area. Buildings and structures in urban areas are known to affect significantly the magnitude of wind gustiness. Because of the growing urbanization globally, quantification of turbulent winds in densely-built, urban districts is important to understand the underlying risks of wind damages. We investigate the influences of densely built urban environments on the occurrence of wind gusts in urban districts of Osaka and Kyoto City during the landfall of Typhoon Jebi by merging mesoscale meteorological and building-resolving large-eddy simulations (LES). By explicitly representing realistic buildings and structures in LES, this study examines complex/complicated characteristics of winds within the densely built urban environment. With the successful reproduction of the track and intensity of the typhoon in meteorological simulations, the simulated winds at the boundary-layer top of the LES model are used to quantify the wind gusts in the urban district. The maximum wind gust in the analysis area of Osaka is around 60-70 m/s, which is comparable to the wind speed at the height of about 300 m. Such wind gusts are generated by instantaneous downward momentum transfer in areas of a cluster of buildings with variable heights. Instantaneous wind gusts are further examined in terms of building density and are found to be strongest when the building packing density is moderate. The results suggest that the risks of wind damages would be maximized in urban districts where the building height is inhomogeneous and the packing density is moderate.