Unfortunately, I'm not sure if that's the factor, as I've flown through both ORD and MDW many times and that has been far from anything close..
Though it could be perhaps that Chicago (& DTW) is an exception? I'm probably not qualified to answer that.
ORD and DTW are just grumpy old big cities.
Try CLE, CVG, STL, MCI. Very friendly cities IME.
Same probably goes for other mid-size midwest cities, IND, MKE, MSP, DSM, etc.