You meant to just text your friend - but mistakenly sent that complaint to the entire wedding party you’re in, bride and groom included. Then your car was towed after you rushed to park before an important meeting (that you ended up being late for anyway). Things went downhill from there.
You’ve had a bad week, and you need to cheer yourself up. Luckily for you, there are many places in Chicago with exactly the kind of comforting, delicious food you need right now. Here are 12 of our favorites.
If you’re in such a bad mood that you really just need to be alone, head here. It’s very small inside (with only about 15 seats), so it’s an ideal place for a solo meal. The tonkotsu broth ramen is delicious and very spicy - consider starting with a baseline order of half spice. That is, unless burning your face off will help distract you from that $1,800 cell phone bill you racked up during your trip abroad. Apparently roaming charges do still exist. In that case, go ahead.
Instead of hitting up a drive-thru for a value meal, consider Big & Little’s for some fancier fast food. They have great staples like burgers and fries, but you can also order giant soft shell crab po’boys, sushi grade ahi tuna tacos, and/or fries topped with foie gras. After the week you’ve had, don’t think twice about going for those fries. This is one of our favorite spots around, casual or otherwise.
The person you’ve been dating for months just broke it off with you to be a contestant on the inaugural season of So You Think You Can Kazoo. Time to faceplant into multiple courses of comfort food. Pearl’s Cajun classics, like po’boys and jambalaya, are fantastic, and don’t ignore the pulled pork poutine served on cracklins instead of fries. It’s a casual spot with good energy and solid drinks that will help you forget all about your ex. They’ll probably get voted off in the first round, anyway.
Few things are as consistently great as the Au Cheval burger. It’s the best burger in Chicago, with two griddled patties, cheese, dijonaise, and pickles, all on a buttery bun. When you add bacon and an egg, it’s practically transcendent. The only issue is that you can’t make a reservation here, so plan on using your bad week to guilt your friends into waiting with you. It shouldn’t be too hard to convince them.
It turns out people aren’t as interested in a “Mittens for Kittens” Etsy store as you’d hoped. You’re not upset about the wasted money so much as the lost time - each one of those little mittens took a full day to knit. The best way to handle this is to go somewhere with lots of heavy food and beer, which has been scientifically proven to put anyone (especially anyone from the Midwest) in a better mood. The Publican has both of these things, plus a giant wooden communal table that helps create an environment that’s upbeat but not irritating.
Your ex swore he’d never get married, but you just saw on Facebook that he’s engaged. Also, he used the dog you owned together to help propose. Time to get a little dressed up and go somewhere you can distract yourself with pizza, pasta, and cocktails. Siena Tavern is trendy and always crowded, with giant booths for you and all your friends (but not your new dog, unfortunately). It’s also just a really good Italian restaurant.
You finally bought a condo in the West Loop - and then your company announced they’re transferring you to Omaha. Head to Portillo’s. Italian beef sandwiches are a Chicago classic, and you might as well enjoy them while you can. The River North location is always packed, so we suggest doing the drive-thru and eating in your car. It’s less embarrassing to cry there, anyway.
Remember when you were little and you’d go out for pizza after losing a Little League game? Well, pizza also works on adults. Go to Pequod’s in Lincoln Park for pan-style pies in a sports bar environment. Consuming large amounts of their caramelized-crust deep dish (plus beer) will make you feel like a winner, at least for the night. We can’t guarantee how you’ll feel when you wake up.
Hands down one of the best places in Chicago to go and forget about your problems. It’s so fun in here that you’ll immediately stop worrying about that pile of unpaid parking tickets you’ve been ignoring, at least for an hour or two. You’re here for Mexican small plates, like beef tongue with a spicy peanut sauce or the outstanding pasta with crab and egg. (The tacos and burritos are very good, too.) Whatever you order, you’ll want to stay in the lively, welcoming space for as long as possible - which is easy to do if you have a boot on your car.
Your boss gave the promotion you thought was yours to someone else. RPM Steak is where to go for a reminder that you’re still a corporate force to be reckoned with. This upscale steakhouse has excellent food, and servers who will make you feel important - even if you only end up ordering a martini and a piece of their 14k chocolate cake. (Not a terrible idea.)
There are two reasons to go to this casual cafe in Humboldt Park after a bad week. One is that the food is fantastic - if we had a grandma who lived in the French countryside, we’re pretty sure she’d make the duck frites they serve here. Two is that you’ll see the chef joking with the staff and customers, and before long you’ll start to feel like a regular. The great food and friendly environment here will make it hard to remember why you were ever so upset to begin with.
Your roommates treated the house like Ibiza while you were out of town, and now there’s no way you’re getting the security deposit back. Unlike that destroyed apartment, you are going to leave Bavette’s in better shape (emotionally at least) than when you walked in. This is a French steakhouse with big, comfortable booths, speakeasy-style jazz music, and service that’s always attentive without being intrusive. It’s the kind of spot where you can get a $175 shellfish tower followed by some excellent prime rib. Your roommates might not care about you, but Bavette’s does.