Analysing and depicting in 3D the design and transformations of urban structures have been concerns ever since the nineteenth century, for both historians and urban planners. What exactly is the impact of the digital humanities on the way we use today’s means of investigation? How can we usefully support the analyst’s tasks, by visual means, in the context of historical research and on the large scale of a city? This chapter describes real experiments that were carried out on the city centre of Krakow, former capital of Poland. Through these experiments, the authors consider the fundamental issues of imperfect knowledge in the historical sciences, the need to and constraints of handling ill-defined temporal data, and the necessity to at least complement “classic” virtual reconstruction efforts with visual solutions that better match the nature of the underlying data. The data are a heterogeneous collection of structures that differ in terms not only of morphology and use but also of documentation quality. The authors introduce an approach that is based on the idea that the gap between the historical sciences and information visualisation (via InfoVis) should and can now be filled. They show the potential added value of InfoVis-inspired abstract graphics in supporting analysis tasks regarding the evolution of urban structures, with the hope that this methodological bridge can be a solution particularly in the context of urban analysis.