It seems the more I eat out in Chicago, the less impressed I am by the food. ESPECIALLY the mid/high end stuff. It's so easy to drop a huge wad of money on dinner and come out with maybe one of two things that were excellent and the rest that's an overpriced, resounding MEH. I'm a good cook and my dude is a good cook, I don't want to spend money unless I know it's going to be better or more labor intensive than what I can do at home.
Maybe I'm overly critical (I've spent the past year working as a food writer, and my boyfriend's a chef, so we're a couple of hard to please motherfuckers), but I can't recall being so consistently disappointed by restaurants in the Bay Area or Japan (where I lived for years) or in other great food cities like New Orleans and New York. I don't have a lot of spare cash, so if I spend a lot eating out, I expect something fantastic, and I don't think that's unrealistic. My visits to Chicago prior to moving here, were memorable, but not for the food.
That said, I do think Chicago has strengths as a food city, but it's not fine dining. Chicago rules when it comes to comfort food and basics- ethnic hole in the wall joints (particularly puerto rican and cuban), slavic buffets, street food like the elotes carts, pizza (but even then, there's a ton of shit pizza in this city- I have no idea how Gino's East stays in business), hot dogs (notably Hot Doug's), hamburgers (Kuma's), coffee (Metropolitan and Intelligensia), ironically granola (Milk and Honey) and booze- there are good local breweries and distilleries and great cocktailers. But a few exceptions, yuppy food, brunch, baked goods (so many overpriced bakeries selling bland, dry cupcakes and you can't even get a good donut due to Dunkin Donut's dominance) all suck compared to other cities. I guess it's still the Midwest and there just isn't the same access to good ingredients and sufficient demand to create truly great food. (And I'm sure there are many who would be happy to tell me I'm full of shit, but I am admittedly biased). There's just too much fucking pretense and not enough craftsmanship.