Shrimp & White Wine (credit: Tim & Eric Awesome Show, Great Job!) Generally:
Double IPA with fried anything
Deep & fruity malbec with steak or salmon
King's Ginger with lemon cake Recently: I had a couple of outstanding birthday meals last weekend. Night one, I took myself out to a place in my old neighborhood called Lula Cafe and had a glass by Tami and the spinach cavatelli followed by a couple glasses of really good rye from an insane, torso-sized bottle at a friend's place. His brother's a salesman for a liquor distributor so he's always got something interesting in his bar. Night two, my girlfriend took me out to a place in the suburbs that flies in its fish and meats daily. I had venison (for the first time in years) with squash and sprouts, and a mild but delicious pinot noir, followed by key lime pie and intelligentsia coffee. Hash-tag Chicago.
Chicagoans are the worst when it comes to talking about the food. It's like a bad comedian, always the highest or the lowest and never anything relatable. If you're visiting Chicago, you don't need to go to Hot Doug's and stand in the wind/rain for an hour just to eat a mildly interesting hot dog. Nor do you need to wait two hours or more for a seat at Kuma's (again in the wind and the rain) to eat a mildly interesting hamburger. And if you're visiting Chicago and can swing Moto or Alinea, go for it, but I have a hard time finding the point in spending that much money on food unless you're not just famous, but famously wealthy, which you are not. If you return, do visit Lula. You might have to wait a little while but the staff are incredibly kind, the food is not just consistently delicious but reasonably priced, and the neighborhood you'll be in is one of the better places to have to wait (if you must wait for a meal). Compare this to Hot Doug's, which is adjacent to a mile-long parking lot for the electrical company fleet vehicles and a drab office park. If you're here in the summer and as inclined to drink as you are to eat, go to the Orbit Room. The longer I've been away the less I feel like I have a "top five" as I do a "top two" establishments. Lula's at the top, and Orbit Room's at the bottom. The best patio in the city (that isn't a roof deck, or whatever it is people do downtown) soundtracked by the best tunes. I don't think I've ever had anything here other than the fish tacos with shots and beers, but it still beats a long list of other Chicago bars and restaurants, and I've never had to wait to get in there. If I had to include a third it'd be Longman & Eagle, but they're just a younger, meat-obsessed, haughty version of Lula. I've also heard they don't treat their staff well at all, which is reason enough for me to stay away unless I've been in a pinch (like xmas eve one year). Randolph Street is the test kitchen. If you really, really, really care about food you likely know where to go, but it appears that you didn't, so moot point.
I would say that I do really care about food, though my focus has been elsewhere as I only moved back to the States in the past year. I'm glad that people are paying more attention to what they're eating and the quality of what they're eating, but the whole "foodie" thing kind of bugs me sometimes. I remember as a kid, buffalo wings were just gaining traction, but not many people were preparing chicken wings at home. Thus, the price of chicken wings was dirt cheap. Now they're as expensive as anything. Same goes for soup bones. Now everyone and their ma is suddenly into eating marrow on toast points and what used to be $1.50 now costs $8. It's one thing to enjoy a nice selection of cheese, but it's quite another to look down one's nose at an establishment for serving what that blog/TV show considers to be a poor pairing. Anyhow, thanks for the recommendations. It's kind of up in the air at the moment, but I just might have a long term thing developing in Chicago, so I'll definitely keep your words in mind.