Urban atmospheric flow is characterized by meteorological processes and street-scale perturbations of microclimate wind velocity and air temperature distributions. The Weather Research and Forecasting model (WRF) is applied to investigate the effects of meteorological processes on temperature distribution over the Greater Montreal Area during the 2017 heatwave. The single-layer Urban Canopy Model is coupled with the WRF to estimate the heat fluxes from the canopy to the atmosphere. The mesoscale simulation results provide the boundary conditions for a new city-scale microclimate LES model, CityFFD. This study first validated the WRF model through multiple weather station measurements and the CityFFD model through the literature data, then investigated the impacts of three canyon aspect ratios and three anthropogenic heat regimes, i.e., surface temperature differences, on the boundary conditions setups. The strong anthropogenic heat assumption was applied to modeling the 2017 heatwave for three consecutive days using the integrated model. The transient results show that a difference of ∼4 m/s wind speed could result in a spatial temperature variation of up to 4 °C for the area under consideration. This study shows the importance of microclimate simulations for regional climate models when studying urban heatwaves.