Global warming is one of the most pressing challenges of our time, contributing to climate change effects and with far-reaching implications for built environments. The main aim of this study is to assess the extent to which Annaba city, Algeria, as part of the Mediterranean region, is affected by global climate change and its broader influences. The study investigated climatic shifts in Annaba city, using a multi-step methodology integrating data collection and analysis techniques. Data collection included 23 years of climate data (2000–2023) from Annaba’s meteorological station, on-site measurements of microclimatic variations, and a questionnaire survey. The collected data underwent four main analyses: a time series analysis to describe climate parameters over 23 years, a statistical analysis to predict potential future climatic conditions (2024–2029) and the correlation of various climatic variables using specialized bioclimate tools to highlight seasonal variability, a spatial study of the urban heat island (UHI) phenomenon and perceived climatic shifts, and an analysis of extreme weather events characterizing heat atmospheric events in the context of urban climate change in the Mediterranean region. The findings revealed a consistent warming trend in Annaba city, with prolonged extreme climate conditions observed, particularly in the last four years (2020–2023). Significant temperature fluctuations were emphasized, notably in July 2023, with record-breaking maximum temperatures reaching 48.2 °C, the hottest on record with an increase of 3.8 °C, and presenting challenges amplified by the urban heat island effect, causing temperature differentials of up to 6 °C within built-up areas. Projections for 2029 suggest a tendency towards heightened aridity with a significant shift towards a new climate seasonality featuring two distinct main seasons—moderate and hot challenging. The abrupt disruption of calm weather conditions in Annaba on 24 July 2023 highlighted the influence of atmospheric circulation within the Mediterranean region featured for both anticyclones and atmospheric blocking phenomena on local weather patterns.