I spent a few days in Chicago recently, which wasn’t nearly enough time. These are some of the things I tasted that make me want to go back.
1. Queso Fundido at Big Star
If you have a paperback and an evening to yourself, sit at the bar. Big Star is known for its reassuring selection of bourbon, so take this opportunity to be soothed. Maybe order a Booker’s, rocks, and let it mellow while they melt your cheese. They’ll bring it bubbling, with a spoon and a messy stack of warm corn tortillas. Oh, my friends. This meal will hurt your heart like the love of a stoic man.
2. Smoked Sicilian Manhattan at The Bristol
Smoked Maker’s, Averna Amaro, and Blood Orange Bitters. Like a chilled Manhattan by a warm campfire, but all the atmosphere happens in your mouth. Wizardry.
3. The Mix at Garrett Popcorn
It’s tempting to dismiss this as a tourist thing. It’s also tempting to shove the entire bag in your mouth once you’ve tasted it. “The Mix” has caramel and cheese popcorn, and probably enough butter for your cardiologist to sense a disturbance in the force. If popcorn doesn’t rain to the floor when you undress that night, then we are different people.
4. Pizza at Great Lake Pizza
This is the best pizza available. Try it at least once, and then maybe go somewhere else. I say this because the owner is not a particularly polite guy. Before we stopped by, I had about five locals warn me on the “pain in the ass” factor, and my personal experience backed them. But! The pizza is incredible, handmade with top-notch organic ingredients. It tastes like affection, so don’t look to the staff for love, look to the food. The best plan is to call ahead, place your order, and then take it to a bar up the street that welcomes Great Lake customers. They were plenty friendly there, and they had beer. Win-win.
5. A cocktail at Vincent
While you’re waiting for your pizza at Great Lake, stop by next door. If Briar is tending bar, you won the lottery — let her mix you whatever she wants. Some of the best drinks in town, and believe me I asked around.
I didn’t have time to hit any fine dining while I was there, but what else did I miss? Tell us about your favorite Chicago foods in comments.
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Mighty Girl 
You basically just named some of my favorite places in Chicago. Next time we’ve got to hit up some others together – definitely have some more recommendations.
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Can’t believe it hasn’t been mentioned yet… Hot Doug’s. They have regular dogs… but also things like “Saucisson Alsacienne: Bacon Sausage with Creme Fraiche, Caramelized Onions and St. Paulin Cheese”… for just $8!
Lots more crazy dogs here: http://www.hotdougs.com/specials.htm
There is always a wait, but it is always worth it, and Doug is super nice.
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To the person (rebekah?) who called reading a paperbook alone at a fancy restaurant “pretentious”, I just have to say – Big Star ain’t “fancy,” just fantastic. I say definitely go there alone with a whole stack of novels because conversation with other people will just waste time that would be better occupied eating tacos and drinking bourbon!
And I second the person who said Big Jones – their bourbon/whiskey list rivals Big Star and the five-pepper jam with the cheddar biscuits are to die for.
And, when you do make it back for fine dining, check out Ruxbin. All I have to say is Salted Chocolate Pot de Creme with Bacon Cotton Candy…
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