The author focuses on the urban world to reformulate the question traditionally interpreted in terms of the entrepreneurial freedom of late medieval merchants: even in this context the notion of libertas, rather than absolutely defining the economic action of groups or people, was related in terms functional to their social and political qualities. The analysis of Italian city legislation, in particular of the regulations of the arts and of the market, highlights how the different degrees of belonging to the civitas guaranteed the spaces for economic action and commercial times: full freedom remained firmly in the hands of a few family groups and privileged while in the market squares of Italian cities farmers, artisans and traders and the vast world of subordinate work were destined to remain subordinate actors.