Thermal infrared imaging is a valuable tool to perform non-destructive qualitative tests and to investigate buildings envelope thermal-energy behavior. The assessment of envelope thermal insulation, ventilation, air leakages, and HVAC performance can be implemented through the analysis of each thermogram corresponding to an object surface temperature. Thermography also allows the identification of thermal bridges in buildings’ envelope that, together with windows and doors, constitute one of the weakest component increasing thermal losses. A quantitative methodology was proposed in previous researches by the authors in order to evaluate the effect of such weak point on the energy balance of the whole building. In the present work, in-field experimental measurements were carried out with the purpose of evaluating the energy losses through the envelope of a test room experimental field. In-situ thermal transmittance of walls, ceiling and roof were continuously monitored and each element was characterized by its own thermal insulation capability. Infrared thermography and the proposed quantitative methodology were applied to assess the energy losses due to thermal bridges. The main results show that the procedure confirms to be a reliable tool to quantify the incidence of thermal bridges in the envelope thermal losses.