The focus of this paper concerns the level of service (LOS) of walking facilities, as perceived by pedestrians. This investigation is based on the hypothesis that pedestrians also consider elements of trip quality, apart from components relevant to the traditional approach of LOS calculation (eg path width, pedestrian flow etc.), for their evaluation. This study examines the perceived LOS of two connected pedestrian streets at the Municipality of Kalamaria, a suburban area located at the city of Thessaloniki, Greece. The perceived LOS was estimated through a questionnaire survey, by taking into consideration the following qualitative factors: attractiveness of land use in the wider area, perceived comfort, safety and security, public transport service, parking service, traffic flows and delays, disabled people’s facilitation, pedestrians’ and bicycles’ service. The initial analysis indicated that all of these factors are related with the perceived LOS to some extent. Moreover, an ordinal regression model was developed, for the LOS estimation. The model results identified as the most important factors the gender of pedestrians, the age, the frequency of walking, the comfort, the traffic flows and delays as well as the disabled people’s facilitation.