I'm originally from the chicago area, and i think it's safe to say that chicago is probably the best place to eat in the midwest. Not only are the very expensive restaraunts great, but the affordable ones are as well.
Good food found its was into nearly all of the chicago suburbs from the city, and y ou can find almost anything nearby if you know where to go. the NW indiana region has great italian, greek, indian, japanese, thai, chinese, middle eastern (cool new flavors there, if you're feeling adventurous), LOTS of good mexican food, all in addition to your usual chain restaurants. I can't think of anything that my hometown area needs except a good BBQ place. Mt dad and I used to drive an hour east every other week to pick up BBQ from a roadside shack restaurant that went out of business after about 2 years. There was never a replacement after that.
I go to school in Bloomington IN, now, about an hour south of Indianapolis. Even here in a small town where students make up maybe 40% of the population for the school year months, has ots to offer. 2 decent Thai restaurants, a few good vegetarian places, 2 GREAT italian places, a little place that offers jewish (yiddish? im not sure how that works...) fare, as well as some others. Most of them are pretty unimpressive on the outside, but if you're the type of person that doesn't much care if the restaurant operates in an old 2 BR house, then you'll be amazed by the food once you sit down to eat. Here agin I'd say we're missing a good BBQ place. I also haven't found a good mexican place yet, though there is a tiny noon-4AM taco shop thats pretty great, and some decent tex-mex.