The paper presents the results of a thermal comfort analysis which was carried out in order to investigate the parameters that influence thermal comfort conditions in urban canyon environment. A special computational tool was used for the parametric analysis, so that the degree of influence of each parameter could be examined. Also, a thermal comfort analysis was carried out in order to compare conditions in streets in two different sites, a traditional and a contemporary settlement, using input data from experimental measurements carried out in the two sites. The results are compared to shading simulations and thermal analysis results, as well as to experimental measurements results which have been carried out in urban canyons in the two sites. ► We perform a parametric analysis to investigate thermal comfort in urban canyons. ► We investigate the effect of different parameters on thermal comfort outdoors. ► We investigate the differences between a traditional and a contemporary site.