This is a good topic, thanks for starting the thread.
I think that Chicago has amazing food, due largely to the fact that Chicago continues to attract huge groups of immigrants. These groups fuel restaurants that are "real" and uncompromised (if, of course often lacking in creature comforts). In addition, various other factors including the overall size of the city and (the shrinking) convention business keep the city blessed with higher end eating. We have a lot of good stuff.
That said, I really do not think that Chicago competes with certain other cities when it comes to food. Us hounds are a very small proportion of the eating public in Chicago. It continues to dishearten me that so much more exposure can be given to the mediocre (at best) Arun's over the several great Thai places. Chicago Magazine covered Mexican food a few issues back yet barely scratched the surface of all the interesting Mexican food in Chicago. As a poster and food writer, Leah Zeldes said a while back, there are a lot more of them than us. There is little great interest in the general population, surely not the local food media for all those places mentioned in the first paragraph.
In addition to rarely seeing anyone besides "us" at ethnic places, the other sign that Chicago is a 1/2 assed food town is the lack of two somewhat releated things. First, we have barely any classic restaurants, meaning a restaurant that dates back 75 years or so. There is hardly anything in Chicago to compare to Union Square Oyster House or Galatoires or Tadich Grill. Do not give me Berghoff because that is hardly the same restaurant, or more aptly, it is hardly the same restaurant it was. Second, there is very, very little in the low to mid range that is not ethnic. We are a city that some levels of dining is being very much over-run by chain and corporate places.
New Orleans was mentioned above. THAT is a food town. Sure, you might say, the choices are limited. Thai, Chinese, Mexican, they are nothing like what you could get in Chicago. Yet, in New Orleans, people are pasionate about food. They REALLY like to eat. Everyone is a Chowhound. Interestingly, when I lived there, there was a very, very good Indian restaurant (in the Indian Garden/Tiffin school). There was barely any Indian population there, not like Chicago, but the quality was raised, not like you would get here, to meet the needs of those who actually know the food, but raised to meet the standards of cooking there. More imporant, there are so many neighborhood places in New Orleans, places in the under $20 range that are worth it, that would in Chicago be really special, but there are just restaurants.
Rob