Chicago’s food scene is not for the faint of heart. When I planned our first trip, the first thing I thought about was all the delicious food we were about to eat. The second thing? I’d probably need to pack a big bottle of Tums.
Turns out I was right to worry. We ate like we were on a mission, and I flew home full, a little tired, and with a notes app packed with spots we never got to. Not everything on this list is fancy, but I’d go back to any of these Chicago restaurants, and these are the ones I’d book first.
My Ten Favorite Places to Eat in Chicago
1. Gino’s East
If you want deep dish, Gino’s East is where I’d start. It’s number one on my list. There are two locations in the city, and we went to the original on the Magnificent Mile.
The pizza is hard to fault. The crust has good flavor and texture, the sauce is seasoned well, and the cheese and toppings are balanced, so nothing drowns anything else. Then there’s the room. Red checkered tablecloths, and booths covered in signatures and notes people have left over the years. It feels like a pizza place should. The service was really good too, and that made the whole visit better.
2. Vito & Nick’s
Everyone talks about deep dish, but Chicago does thin crust too. Yes, thin crust exists in America, it just hasn’t taken off. Vito & Nick’s is the exception. They’ve been at it since the 1950s, a neighborhood pizzeria that does thin crust and does it properly. Go here when you need a break from deep dish.
3. Athena
Athena is a Greektown classic. Or West Loop, depending on who you ask, since the whole area has blown up and nobody agrees where one ends and the other begins. Whatever you call it, Athena isn’t going anywhere.
It’s reasonably priced, and there are staff everywhere. Total chaos, and I love it. They blowtorch the cheese right in front of you, and it’s one of the best appetizers in Chicago. Take a date and act like you’ve been before. It’ll beat most of the trendy places on any list.
4. Gene & Georgetti
Classic steakhouse, and I really mean classic. The waiters have been there forever, the average age is probably 77, and you won’t see a single notepad. It’s a joint, in the best way. Nothing has changed since the day it opened. You’ll find it tucked under the Merchandise Mart L tracks, and you won’t find anything more old school.
The steaks and chops are premium, they’d have to be to last this long in Chicago. The sides are gigantic. And the crowd is great for people watching. One Saturday, the couple sitting next to me turned up next to me again the following weekend at Gale Street Inn. They were in their 70s. It was one of the most validating experiences of my life.
5. Mazor
From the outside, Mazor looks like any other counter-service taco place. It’s not. This West Loop Mexican-Guatemalan spot is all about masa, and the nixtamalized corn is behind everything on the menu.
The tortillas are fluffy and made fresh in-house. I had them with ribeye and crispy potatoes, but the shrimp ones with chipotle mayo are just as good. Then there are the tostadas, with raw tuna, smoky salsa macha and edible flowers on top. The chicken tinga empanadas and the chorizo tetelas use masa too.
You can grab your food and leave, and a lot of people do. I’d sit down and eat it there.
6. Oriole
This is our highest-rated restaurant, and yes, it’s expensive. Birthdays, date nights, special occasions, this is the place for it.
You get in through a freight elevator that doesn’t work, in an alley in the West Loop. Sounds strange, but the vibe inside is relaxed, not stuffy at all. The servers tell you what you need to know about each dish and then leave you alone. The truffle pasta might be the one that finally convinces you truffles aren’t a scam.
The foie gras course is my favorite part. It’s a billowy foie mousse with blueberries on toasted brioche, and for this one they move you to a counter seat right in front of the open kitchen. I can only assume the chefs want to see your face when you take a bite. I would too.
7. Portillo’s
Portillo’s has a great Italian beef sandwich, but the real reason I love it is the Chicago dog. It’s my favorite in the city. They have a jumbo dog option for extra hot dog flavor, the toppings are balanced, and the bun is solid enough to hold everything together.
Walking in feels like wandering through a neighborhood street in 1930s Prohibition-era Chicago. It’s busy, loud, and fun, and a good way to eat the classics.
8. Santa Masa Tamaleria
In Chicago, you can run into a tamale almost anywhere: restaurants, sidewalk pop-ups, or some guy with a cooler going from bar to bar at midnight. The ones at this casual Mexican spot in Dunning are better than all of those. They’re smooth, buttery, and so fluffy they’d make clouds jealous.
Grab a seat at the long diner-style counter and try the poblano and salsa verde tamale, the chicken in smoky guajillo sauce, or the dessert tamal with strawberries and caramel. Leave room for the cheesy, meat-filled Santo taco or the enchiladas. They’re made with the same excellent masa, and they’d get even lifelong Midwesterners excited about corn again.
9. Avec
When all else fails, go to Avec. The food at this West Loop Mediterranean small-plates place always makes me happy, especially the bacon-stuffed, chorizo-wrapped dates and the taleggio flatbread.
The communal dining room feels like a wooden shoebox, so you’ll probably be sitting elbow to elbow with strangers. They’re having a great meal too, so it works. It’s a good spot for a birthday, or for your 76th date with the person you share a Netflix account with. Go at least once a year, just to remind yourself how reliably good it is.
10. Loaf Lounge
Loaf Lounge is now my favorite place for a Chicago breakfast sandwich. I can’t do spicy, and in my search for a good spice-free breakfast sandwich, most of them end up dry. Not this one.
They have a handful of options, and my go-to is simple: bacon, eggs, and cheese on a soft seeded bun with a little herby mayo. It all works together. There’s always a line out the door, which tells you something. I still need to go back and try the lunch menu, because it looks amazing.
