In recent decades, global climate change and rapid urbanization have aggravated the urban heat island (UHI) effect, affecting the well-being of urban citizens. Although this significant phenomenon is more pronounced in larger metropolitan areas due to extensive impervious surfaces, small- and medium-sized cities also experience UHI effects, yet research on UHI in these cities is rare, emphasizing the importance of land surface temperature (LST) as a key parameter for studying UHI dynamics. Therefore, this paper focuses on the evaluation of LST and land cover (LC) changes in the city of Prešov, Slovakia, a typical medium-sized European city that has recently undergone significant LC changes. In this study, we use the relationship between Landsat-8/Landsat-9-derived LST and spectral indices Normalized Difference Built-Up Index (NDBI), Normalized Difference Vegetation Index (NDVI), Normalized Difference Water Index (NDWI) derived from Landsat-8/Landsat-9 and Sentinel-2 to downscale LST to 10 m. Two machine learning (ML) algorithms, support vector machine (SVM) and random forest (RF), are used to assess image classification and identify how different types and LC changes in selected years 2017, 2019, and 2023 affect the pattern of LST. The results show that several decisions made during the last decade, such as the construction of new urban fabrics and roads, caused the increase in LST. The LC change evaluation, based on the RF classification algorithm, achieved overall accuracies of 93.2% in 2017, 89.6% in 2019, and 91.5% in 2023, outperforming SVM by 0.8% in 2017 and 4.3% in 2023. This approach identifies UHI-prone areas with higher spatial resolution, helping urban planning mitigate the negative effects of increasing urban LSTs.