[the urban politician]

^ Spot on, LVDW.

The issue Chicago deals with is that it really is such a great city which is so under recognized. Hell, the city right now even is changing at a whirlwind pace. It's hard for its reputation to keep up with what is happening. If you aren't on the ground here you will just expect a glorified Cleveland. Chicago needs to do away with this perception problem for once and for all with a dedicated, expensive global marketing campaign.