Impervious pavement surfaces within urban areas present serious environmental problems due to waterlogging, flooding and in particular, the urban heat island (UHI) phenomenon. Another issue that has recently been highlighted is user comfort in pedestrian and cycling areas. Materials that have potential for overcoming these issues include pervious concrete (PC), a new type of construction material with improved drainage properties and thermal properties. In this study, the thermal properties and behavior of commonly used concrete paving materials in urban areas (dense concrete (DC) and concrete pavers (P)) and pervious concrete (PC) paving flags were investigated and compared in terms of their thermal properties. Material behavior under different temperature conditions was investigated within laboratory research measuring thermal conductivity (λ) and the capacity for heating and cooling using infrared lamp. Complementary to laboratory tests, field research was conducted analyzing the surrounding conditions on pavement wearing course behavior under real weather conditions. Dense concrete paving material had the highest thermal conductivity coefficient and heat absorption capacity, and slowest heating and cooling speed, compared with the other paving materials. The results also highlighted the similar thermal properties of PC and P but with potentially improved user comfort for PC due to its draining properties. The base layer and surrounding characteristics had a significant influence on the thermal behavior of pavements, and future research should consider these parameters when addressing the UHI effect for different paving materials.