[LouisVanDerWright]

Yup, the freeze thaw doesn't gurantee terrible road conditions. Much of it has to do with what is underneath and, beyond what viva said about quality of construction, how it has been disturbed over the years.

The issue Chicago has on many streets is that you have a century of layers of road surfaces on top of roads that were already raised up out of the swamp by 7-10 feet often using sand from dredging the lake. Then you have 100 years of cuts for utilities to properties being patched properly or not. Then you have heavy industrial traffic throughout the city hammering those repairs that are already sitting on who knows what kind of roadbed which is sitting on what is literally embankments made of sand.

Given those challenges I would say Chicago's road infrastructure stays in remarkable shape. You can definately see the effects of freeze thaw (i.e. the roads are peppered with craters from Feb-Mar), but the majority of even that damage seems to occur predictably where the roads have been disturbed or damaged from utility cuts. Despite the challenges, most apocolyptic streetscapes are quickly addressed by the city. Unfortunately resurfacing only does so much when you have an asphalt patch next to cobblestone next to a concrete patch all overlaid by 2" of asphalt. That will only take a pounding from so many 18 wheelers before you will see the patchwork patter reemerge.