Weird - I visited Chicago a couple years ago from NYC and was shocked at how pedestrian-unfriendly central parts of Chicago seemed (e.g. River North). There were parking lots everywhere, with aggressive drivers pulling in and out. I walked through a parking lot to go to a liquor store and was almost run over. Sometimes crossing a large street felt like a race against the green light. Jaywalking signaled to drivers that they should speed up, which is the mark of a driver-run city IMO.
The whole experience contrasted heavily with the east coast cities like DC, Baltimore, Philly, NYC, Boston. Maybe it's changed in the last few years, though.