The First Timer’s Guide To Eating In Chicago

You’re in Chicago for the first time ever. You’ve got 72 hours and an appetite for everything. Where do you start?

That’s a question we get asked a lot, and it’s a hard one to answer. But we’re gonna try so that you don’t return home having only sampled our finest mozzarella sticks from the food court at Navy Pier.

There’s no doubt you’ll spend time wandering up and down the Magnificent Mile and checking out the West Loop. And while there’s great food there (some of which is on this list), don’t confine yourself to eating all your meals in these areas—you’ll miss some of the best restaurants in the city.

This isn’t meant to be a definitive list of Chicago’s best restaurants—it’s just what we’d do if we were in your shoes. Speaking of shoes—hopefully you brought something comfortable. You’ve got a lot of ground to cover.

THE SPOTS

Bavette’s is our favorite steakhouse in Chicago. First, because the actual steak is delicious. Second, you can come here, not order a steak (entrees like the fried chicken and the pork chop are outstanding), and still have a fantastic meal. Third, the 1920s jazz music playing in the windowless dining room makes this place feel like it exists outside of the normal space/time continuum. Which is convenient, because to get a reservation at a decent time you should have made it about 100 years ago.

You may or may not know it, but Chicago has an absurd number of Top Chef alums. One of them is at Monteverde in the West Loop, which also happens to serve some of the best Italian food in the city. It’s reasonably priced, nice but you don’t need to get dressed up (unless you want to) and every pasta dish is fantastic - especially the cacio e pepe. If you want to try the ragu alla napoletana (a giant plate full of fusilli, sausage, meatballs, and a large braised pork shank), just plan on trying to stuff the inevitable leftovers in your hotel mini-fridge.

Need a brunch spot? Go to Kasama. Looking for a great tasting menu? Kasama. Whatever the meal, this Filipino cafe/fine-dining hybrid needs to be a part of your Chicago itinerary. During the day, they have options like an incredible longanisa breakfast sandwich, and an arsenal of pastries that’ll transform an oversleeper into a morning person. At night, the narrow restaurant is softly lit, setting the mood for a $235, 13-course dinner, with dishes like umami-packed mushroom adobo with mussel emulsion and pear granita halo halo. It’s a tough reservation to book, but it’s worth planning 45 days out and waiting for the Resy page to go live at midnight—or else you might have to stand outside and hope for Kasama scalpers. 

This River North spot looks like a typical white-tablecloth French restaurant. It’s not. Obelix expertly walks the tightrope of feeling formal without being stuffy. And that same balance is present in its menu, which is filled with a mixture of classic dishes like escargot and beef wellington, as well as playful, fusion-y ones like the foie gras-filled taco. Yes, we know the squab pithivier on the menu might say Serious French Restaurant, but it’s counterbalanced by a hip-hop playlist, and attentive servers who are chill enough to crack a few jokes.

Lem’s has been around since 1951, and is probably the barbecue restaurant your uncle who has visited here exactly once knows about. History aside, this iconic spot in Chatham makes some of our favorite barbecue in the city. The ribs are aquarium-smoked (a method unique to the South Side of Chicago) and the sweet, vinegary mild sauce (also unique to Chicago’s South Side) is a perfect counterpart to the fatty meat. Also, the ribs come on a bed of fries that soak everything up, which is just wonderful.

We probably don’t need to tell you that Chicago is known for deep dish pizza. And if you’re here for the first time, you absolutely need to try some. But where to go? Start with Pequod’s in Lincoln Park. They serve pan-style deep dish with a “caramelized” crust (a.k.a. the burnt edges of crispy cheese around the outside of the pie). These pizzas are delicious, to the point that a meal here might start a decades-long feud between you and your friends in New York.

Yes, deep dish is the type of pizza that Chicago is known for. But much like how Queen’s “We Will Rock You” was originally a B-side to “We Are The Champions”, Chicago’s legendary cracker-style thin crust can’t be ignored. And that’s what you’ll find at Vito and Nick’s in Ashburn. This place has been around since the 1950s and is an institution worthy of the Chicago Pizza Hall of Fame (which doesn’t actually exist, but probably should). Their pizza is super thin and crispy, with bubbly browned cheese and a spicy tomato sauce. Inside, it’s a total dive: drop ceilings, neon beer signs, and wood-paneled walls. And we hope that never changes.

This iconic family-run Italian deli and sub shop in the West Loop has been around since 1937, long before the West Loop was the Disney World of restaurants. The industrial-looking exterior hasn’t changed since the neighborhood was full of meatpacking warehouses, and inside they’re making some of the most delicious Italian subs and sandwiches in the city.

After visiting Chicago, you can count on people asking you about deep dish and the burger at Au Cheval. So when you interrupt them to talk about the momos at The Momo World, a casual counter-service spot in University Village, they’ll be surprised. But it’s your sacred duty to spread the word about the fantastic dumplings here. There are a lot of different preparations, including the classic steamed, jhol (served in a spicy soup), and creative options like the momo chaat or tandoori, which are steamed, fried and then grilled. They’re all delicious, and each order is under $14. So, spread the good news.

It’s in the Chicago Constitution that you can’t leave the city without visiting at least one steakhouse. For a classic Chicago steakhouse experience, go to Gibsons in the Gold Coast. It’s the most iconic one, encompassing all the things people love about these institutions: great steaks, great sides, an entire section of the menu devoted to potatoes, and attentive service. It feels a little dated, but in a charming way, and despite the fact that it’s in the Gold Coast, it isn’t too stuffy. The crowd’s a mix of regulars, tourists, and locals celebrating birthdays or anniversaries with (literally) six-pound desserts that will absolutely have to be placed in checked baggage at the airport.

5 Rabanitos in Pilsen is one of our favorite restaurants for showing off Chicago’s great Mexican food scene. There’s no wrong way to order here—get the tacos, anything from the huge vegetarian menu, the carne asada, or the very spicy ahogada torta. The menu is long, and the service is so friendly you won’t want to leave. Even when they (very politely) ask you to because they’re closing for the night.

If you tell someone you’re coming to Chicago, they’ll probably tell you to go to Au Cheval in the West Loop—whether or not they live here. And they’ll be right. This place has the best burger in Chicago (maybe even the best in the entire country). They don’t take reservations and it’s always crowded, so plan on killing time. The Lone Wolf next door is handy for this purpose. When and if you do get a table, plan on friends and family asking if the burger “lives up to the hype.” It does.

Daisy’s is our favorite Hyde Park restaurant. With a busy dining room filled with jazz people eating great food and drinking Hurricanes, this casual New Orleans-inspired spot improves our mood more effectively than a subscription to Headspace. There are plenty of tables for groups of all sizes, plus a bar that’s perfect for dining solo. And considering it’s from the same team behind Virtue, a fantastic Southern spot down the street, it’s not surprising that the gumbo and fried chicken at Daisy’s are delicious. But the best things here are their po’boys. Whether you get the shrimp, roast beef, or fried green tomato, when sandwiched between their crackly bread imported from New Orleans, you’ll hardly notice you decided to visit when it’s 25 degrees outside.

This spot in Lakeview is perfect for a weekday breakfast. It’s great on the weekends, too, but it tends to get slammed, so take advantage of a calmer morning if you can. Everything here is made in-house, and tastes like it - we particularly like the grown-up pop tart and the bread pudding pancakes. Get some baked goods to go, too. They’re ideal for late-night snacking at your hotel.

Chiu Quon in Chinatown is the original location of this classic Chinese bakery (the other is in Uptown). And though we love them both, we can’t think of a better place to stop for a snack while walking around Chicago’s Chinatown. Anything from their pastry case will be delicious, such as the pork buns, sponge cakes, sesame balls, egg custards, and much more. Plus, everything is made fresh daily. It’s cash only, so be prepared.

You’re in town for a wedding—instead of doing a hangover brunch at some spot downtown, consider heading to QXY in Chinatown instead. It’s nice and casual (the interior looks like it came from a Swedish design magazine), and specializes in delicious broth-filled dumplings you can get steamed, boiled, or fried. You’ll see the kitchen making everything to order, which is way more entertaining than the three-hour-long ceremony you had to endure. Try and bring a group so you can order as many combinations as possible.

If you want to go someplace you won’t find advertised in the back of a taxi, consider the Edgewater location of Huaraches Dona Chio, a tiny cash-only garden-level spot on a quiet side street of the North side neighborhood. You should definitely order the namesake huaraches, but anything here involving their housemade masa is delicious. You get to pick your toppings (with options like pastor, steak, or calabaza) plus your salsa (red or green), and there’s really no wrong decision. There are only six tables here, but if you’re visiting in the summer, you can eat on their cute side patio.

Italian beef sandwiches and hot dogs are almost as important as pizza in Chicago, and the Portillo’s in River North does both very well. And yes, Portillo’s now has multiple locations, but it started here—so as far as we’re concerned, it’s a must-stop. Make sure you get both a hot dog and an Italian beef, and if you know to order a chocolate cake shake, too (which now, you do), you’re basically a Chicagoan already.

This is one of the most famous restaurants in the world, and its tasting menus can cost anywhere between $200 and $500 per person. So you definitely need to plan ahead if you want to come here. Your meal won’t just be expensive—it’s also guaranteed to be pretty dramatic (expect lots of theatrics, like edible balloons and fog machines). In other words, dinner here feels like a once-in-a-lifetime experience. And yes, we realize that’s a lot of pressure to put on a restaurant.

If you’re looking for a fun, casual restaurant with great food and service, you’ll find it at Giant in Logan Square. The food at this little restaurant is, to put it simply, f*cking fantastic. To put it less simply: you’ll find interesting and complex dishes like perfectly seared scallops on top of crispy masa with oranges and cotija. Or, roasted peppers, aged provolone, and everything-seasoned butter served with anchovy bread that—when combined - tastes like a Tostino’s pizza roll, but in the best way. The narrow restaurant recently added plexiglass between the tables, but they also have a charming back patio, too.

Triple Crown is a Chinatown staple, an iconic and incredibly busy dim sum spot on Wentworth. Located on the second floor, it’s not uncommon on weekends to see a line of people waiting for a table. But the good news is that busy crowds mean fresher dim sum, and this place takes reservations. Classics like BBQ buns, shrimp dumplings, and beef rice crepes are all solid, and the sweet custard buns in the shape of cartoony pigs are great for people with cute aggression.

Daisies is a Midwestern pasta-focused restaurant in Logan Square. And while “Midwestern pasta” might conjure up nightmares of things like tuna noodle casseroles, here it means delicious non-Italian pastas made with local ingredients. The menu feels inspired by your friend who has a (successful) garden, with seasonal dishes like a fantastic beet agnolotti, or the gnocchi made with pickled chard and bacon. Basically, it’s exactly the kind of farm-to-table place that will make a visitor realize we’re in a city surrounded by actual farms.

We look for every opportunity to tell people to order Sun Wah’s Peking duck feast—it comes with baos, a choice of fried rice or noodles, and a light soup made with the bones from the carved duck. So what better excuse to come to the casual spot in Uptown than when being in Chicago for the first time? There’s plenty of room for groups in their bright two-story dining space, and sharing a whole roasted duck is an ideal group activity.