In this paper we introduce a comparative study on three streets’ intelligibility. The study objects are Trollebergsvägen, Karl XI gata and Öresundsvägen in Lund, Sweden. Öresundsvägen is under negotiation for development in coming years. Here, there will be a variety of building structures allowing mixed social groups to live side by side and also businesses established close to the inhabitants. We have used the quantitative method Space syntax and the qualitative data of case studies to measure the intelligibility of these streets. Since Bill Hillier has found a correlation between integration and connectivity to affect the intelligibility that local and global streets produce, we will compare Space syntax analysis with the qualitative case studies in order to investigate and evaluate Hillier’s claims. In doing so we do two Space syntax analysis of integration and connectivity of the city with tables showing values for the streets. Results of this study shows that these two types of analysis would give a better understanding of intelligibility when are used.