The application of the network approach to the urban case poses several questions in terms of how to deal with metric distances, what kind of graph representation to use, what kind of measures to investigate, how to deepen the correlation between measures of the structure of the network and measures of the dynamics on the network, what are the possible contributions from the GIS community. In this paper, the authors addresses a study of six cases of urban street networks characterised by different patterns and historical roots. The authors propose a representation of the street networks based firstly on a primal graph, where intersections are turned into nodes and streets into edges. In a second step, a dual graph, where streets are nodes and intersections are edges, is constructed by means of an innovative generalisation model named Intersection Continuity Negotiation, which allows to acknowledge the continuity of streets over a plurality of edges. Finally, the authors address a comparative study of some structural properties of the networks, seeking significant similarities among clusters of cases. A wide set of network analysis techniques are implemented over the dual graph: in particular the authors show that most of the considered networks have a broad degree distribution typical of scale-free networks and exhibit small-world properties as well.