Over the past two decades, the joint manifestation of global warming and rapid urbanization has significantly increased the occurrence of heatwaves and the formation of urban heat islands in temperate cities. Consequently, this synergy has amplified the frequency and duration of periods with tropical nights (TNs) in these urban areas. While the occurrences of such extreme events demonstrate irregular and nonlinear annual patterns, they consistently manifest a discernible rising decadal trend in local or regional climatic data. In urban regions situated amidst hilly or mountainous landscapes, changing wind directions—often associated with uphill or downhill thermal flows—profoundly impact the spread and dispersion of heat-related pollution, creating unique natural ventilation patterns. Using the Lausanne/Pully urban area in Switzerland as examples of hilly and lakeshore temperate cities, this study explores the influence of wind patterns and natural urban ventilation on the nonlinearity of recorded climatic data within an urban environment. This study integrates a mesoscale numerical weather prediction model (COSMO-1), a microscale Computational Fluid Dynamics (CFD) model, field observations, variational mode decomposition technique, and statistical analysis to investigate how wind speed and direction critically influence the nonlinearity of recorded long-term trends of extreme events, specifically focusing on the frequency and duration of TNs in lakeshore and hilly cities. The results strongly indicate a direct correlation between the frequency of TNs and the occurrence of specific moderate wind patterns. These wind patterns are exclusively captured by the microscale CFD model, unlike the mesoscale model, which neglects both urban morphology and complex hilly terrains. The impact of temporal and spatial variability of the wind field on long-term observations at fixed measurement stations suggests that caution should be exercised when relying on limited spatial measurement points to monitor and quantify long-term urban climate trends, particularly in cities located in complex terrains.