If you are looking for some nice European shots of dense urban living, try the Amsterdam and Rotterdam sections here:
http://www.iruditek.com/hedaweb/mod_hedavisor.php
Having visited these places myself, i am amazed at just how densely populated a place like Holland actually is nowadays. But also how nice a place it can be to experience, despite of the densities. In the other old Italian medieval photo collections, you can compare the extremely dense medieval urban environment of pedestrianisation with the broader streets and public areas in your Chicago collection. In fact, without seeing Hector's great couple of shots of Ravena streets, i simple would not have ever believed that streets could be that narrow! I don't think any city in the whole world though, is as interesting from a point of view of bridges, and their relationship with the city, as the city of Venice is. Normally in our Western culture bridges merely become objects of infrastructure - scaleless and designed to get the most cars over the river as possible. The pedestrian is nowhere in the picture at all.
Sometimes you have to go back to the time before mechanisation to find out what pedestrian movement should be all about. In fact, i would be very interested in seeing your photos, Jordan, if you were to travel around Europe some time. Of course, there are others parts of the world too, of which photographers have given time and energy to. My post here includes links to places like Mexican peasant villages, Japanesse spooky dereliction and so on.
http://www.archiseek.com/content/showthread.php?threadid=2039
If you have Quicktime 6.0 installed, i am sure that i liked a couple of VR websites too. The Dutch photographers Dennis Bouma / Monique Westerhof have absolutely brilliant views of urban life in Vietnam and the Phillipine Islands. A density of urban population, that could be very similar to the medieval cities of Europe in their heyday.
Check out some real dereliction, chaos and abandonment in 'Lost in America' or Spooky Japanesse dereliction web sites. Weither it is a motel straight out the Vampires movie, lost in the vastness of Americas mid-west. Or the passing of old regimes, old infrastructure, old religions in Japanesse Islands - i think your 'ugly' Chicago stuff loves quite good by comparison.