Urban microclimatic heterogeneity shapes plant phenology, morphology, and reproductive expression, relevant for planning and management of sustainable urban green spaces. This study examines how contrasting urban settings influence flowering dynamics and floral morphological traits of Chaenomeles × superba ‘Pink Lady’ in Novi Sad (Serbia). This research was conducted from 1 January to 8 April 2025 across a representative street and a park environment, differing in degrees of thermal exposure, solar radiation, and environmental buffering typical of urban landscapes. Flowering phenology was monitored through field observations using the BBCH scale, recording the beginning of flowering (BBCH 60; more than 10% of flowers open), full flowering (BBCH 65; more than 50% of flowers open), and the end of flowering (BBCH 69; more than 80% of flowers faded). Monitoring was conducted every second day until the beginning of flowering and daily until the end of flowering. Floral morphology was assessed during peak flowering by analyzing 50 flowers from each analyzed individual. Measurements included sepal and petal length, flower diameter, number of petals, stamens and pistils, and the number of fertile carpels. Data were analyzed using descriptive statistics and comparative statistical tests. The results reveal clear differences in flowering dynamics between urban contexts (street-like and park-like settings). Flowers in more exposed urban areas exhibited an earlier onset of flowering, a faster progression to full bloom, and a shorter overall flowering period, whereas plants in buffered green environments showed prolonged flowering and more gradual phenological transitions. Floral morphological traits also varied between environments, with flowers in park-like settings displaying larger dimensions and more pronounced floral organs, while several traits remained consistent across settings. This study demonstrates that urban microclimatic conditions strongly shape flowering dynamics and reproductive traits of ornamental plants, emphasizing the importance of microclimate-sensitive species selection for sustainable and resilient urban green spaces.