The show is just badly done, plain and simple.
Even looking at Chicago, the only damage that's been done that I can recall off the top of my head comes from the ridiculously overgrown plant life or crashed trains (why they crashed, I have no idea; though I could be misremembering a massive wreck) and airliners. All the windows and doors in the buildings we've seen were in place. There were no signs of large fires or riots. Cars, when we saw them, were just abandoned and maybe had their doors left open. But beyond that, no real signs of the chaos that should and would have occurred. Hell, the only violence we've seen in flashbacks have only involved one or two people.
The fact that the people at Monroe's base actually were
just sitting pretty and doing nothing while "waiting for orders" is the biggest WTF of them all.