Before I launched The Takeout, I was a longtime food writer for the Chicago Tribune. When you have a job like that, invariably, you’d get asked a lot about restaurant recommendations. An e-mail I’d receive on a weekly basis is: “Where should a first-time Chicago visitor eat while in town?” I’d answer this question so many times, eventually I wrote it down on a Google Docs and just copy/pasted the answer to save five minutes of typing. Then Twitter came along and the same question persisted, so I ended up pinning the response atop my profile page.
My current job means I don’t write about Chicago restaurants as much anymore. But even though The Takeout fancies itself as a national publication, our roots are firmly, proudly in Chicago. (It was a conscious decision to base our operations in the Midwest, which we’d like to think offers a different geographic perspective from many of our food media colleagues. And anyway, we could actually afford to buy a place here.) Even after all these years, the question comes up a lot: I’m in Chicago for a quick visit, what are the restaurants I absolutely must hit up?
As always, I’m happy to answer.
A few notes before we start
- These are not necessarily “the best” restaurants in town. These recommendations don’t necessarily cover slowly dying culinary traditions that I feel are important to keep alive. I base this list on a few assumptions: You’re staying within a three-mile radius of Chicago’s downtown “Loop” area, and your main mode of transportation is public (train, bus) or Lyft/Uber, and you don’t intend on traveling more than 20 minutes to the food destination. I’m not trying to score originality points: These are places that have reliably delicious food.
- Look, I get the appeal of deep-dish pizza, because that’s what decades of a powerful marketing lobby has callused into the minds of non-Chicagoans. I hate to break it to you: It’s tourist food—not that tourist food can’t be delicious—but it’s a dish most Chicagoans stay away from. Yes, I understand there’s an Instagram feed that needs to be fulfilled; there are ‘likes’ to validate your existence. Tell you what: We have a subscription to iStock, a stock image service. You have my permission to use this photo below of a thick “Chicago-style” deep dish pizza—a picture we’ve already paid for!—that you can use to your social media heart’s content. Take this photo, and skip the deep dish places.
9 a.m. — Tortas Frontera/Xoco
You arrive at O’Hare International Airport first thing in the morning (sorry, Midway passengers). I hope you’ve landed in Terminals 1, 3, or 5, because that’s where you’ll find Tortas Frontera, the Mexican sandwich shop from Chicago Chef Lord Rick Bayless (it’s become a minor tradition to post pictures of your torta on social media if you’re passing through O’Hare). The sandwiches here are legit—the choriqueso in particular is a crunchy, crispy, gooey mess of chorizo, poblano peppers and melted Jack cheese. Bayless’ flagship restaurants can be tough to get into, but the tortilla soup and guacamole at Tortas Frontera uses the same recipes, and they are deeeelicious, people. (Xoco is located in the River North neighborhood of downtown Chicago, and is essentially an expanded sit-down version of Tortas Frontera. If you get there early, get churros and a cup of thick Mexican hot chocolate. Xoco is closed on Sundays and Mondays.)
11 a.m. — The Purple Pig
Consistently one of my favorite restaurants in town, The Purple Pig takes its namesake meat and transforms it into a multitude of forms: spreadable, cured, thin-sliced, potted, sausaged, to name a few. If you had to Zagatifiy the restaurant into a few words I’d say “Mediterranean small plates,” but really it’s the type of place you order a plate of cheese, a plate of cured meats, 3-4 plates of everything else, a bottle of Grenache, and just sit there and eat and laugh for 90 minutes straight. Three of my favorite dishes here have remained on the menu since day one: crispy chicken thigh kebabs, milk-braised pork shoulders, and the charred broccoli, which you will proceed to eat and want to immediately learn to make the anchovy vinaigrette dressing. Friends, that recipe is right here.
2 p.m. — Portillo’s
If you really want a Chicago cliche, skip the deep dish and opt for the far-more delicious and ubiquitous Chicago-style hot dog and Italian beef. Chicago hot dogs are a specific assemblage of ingredients: A steamed/boiled wiener nestled in a poppy-seed bun, topped with tomato slices, mustard, a dill pickle spear, sport peppers, diced onions, neon green relish, and celery salt. It’s a crunchy, sweet, briny, altogether delicious hot dog that, for a humble street food, is surprisingly complex. Then there’s the Italian beef sandwich—a messy, wet mound of shaved beef between bread—worth tasting if only for a condiment rarely found outside the Midwest: giardiniera. This is an oily and peppery bricolage of chopped pickled peppers, carrots, celery, and cauliflower, somewhat related to the olive salad found on muffuletta sandwiches. Portillo’s is the largest of the Italian beef/Chicago hot dog chains, and as such, they’ve mastered the making of those sandwiches into a science. (If you dare, request the Italian beef/sausage combo, because you haven’t really lived.)
4 p.m. — Garrett Popcorn
So far you’ve eaten a Mexican torta, several plates of cured/roasted meats, cumulatively about a half gallon of olive oil, and two of Chicago’s most famous sandwiches. What you really need now is an afternoon snack. Garrett Popcorn is home to the cheese-and-caramel popcorn combo—there’s nothing more to add besides a freshly made batch is incredibly unhealthy for you but also incredibly tasty. You can always buy a tin and take it home to grateful loved ones.
6 p.m. — The Publican
There are some 6,000 restaurants in the Greater Chicago area, and The Publican is the one I recommend most often to friends coming into town. I’ll link to their menu and let one passage from their cookbook describe the restaurant:
“Big piles of brown stuff.” And what wonderfully delicious stuff it is. (I also made their porchetta recently and it might have been one of the two best things I’ve ever cooked.) Best bets: A big plate of their bread, farm chicken, “ham in hay,” barbecue carrots, whatever seafood they recommend.
9 p.m. — The Aviary
A cocktail bar for James Bond if he fell down the rabbit hole and into Alice’s Wonderland. The drinks creations here, to state baldly, are awe-inspiring, and upends your expectations of what the theater of after-dinner drinks could entail. As expected of a place from the team behind Alinea and Roister, The Aviary is not a lounge you can stroll into, even on a weekday night—actually, forget about walking in. This and The Publican are my only recommendations where you’ll need to book several weeks in advance.
11 p.m. — La Pasadita
Is it possible that you still might be hungry? If so, come here for some bodacious carne asada tacos or three, a basket of chips and salsa negra, and a frosty bottle of Mexican Coke. That sounds like a fine night cap to a delicious day in a pretty cool city.