No, you don't have to go into Chicago to get a decent meal. Reading these boards gives you the impression that it does. That is probably because most of the participants live in the city and hang around in the city. There is also a critical mass of restaurants in the city.
I have had some good meals in the city and some terrible ones. I have found that some of the recommendations have NOT been as good as some of the places that I have stumbled into. I have found some places that certain people do NOT like that I have really enjoyed.
Personally, Midas, I lived in the Cleveland area for five years and after the first, we generally ate at home because the quality of the restaurants in the under $25 range was pretty bad (but there were some good pizza places) and not anywhere near what I could produce at home.
But personally, I would rather head to Woodman's and get a frozen pizza before heading to Gino's East again. And if I see another bottom round (oops, I mean Italian Beef) sandwich, ...