You’re in Chicago for the first time ever. Where do you start?
There’s no doubt you’ll spend time wandering up and down the Magnificent Mile, and checking out shops in the Gold Coast. 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. Also, prepare for it to be unbearably cold or unbearably hot. That’s what life as a local is all about.
This isn’t meant to be a definitive list of the city’s best restaurants, but we think it’s a good beginning.
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 not fancy, 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 going to bed early.
Lincoln Park isn’t exactly a hot neighborhood. In fact, it definitely falls into the “old news” category. But Galit is one of the newer spots in Lincoln Park, and one of the most exciting in the city. It’s a Middle Eastern small plates restaurant with across-the-board great food, from the creamy hummus (the one topped with brisket is fantastic), to roasted carrots, to a rich and spicy shakshuka. The large dining room works well for both groups and dates. It can be hard to reserve a table, but the bar is walk-in only and is absolutely worth a try.
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 fancy or 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 our favorite restaurant 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.
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.
If you’re a first-timer in Chicago, there’s a 99% chance you end up in the West Loop at some point during your trip, and a 98% chance of eating at a restaurant in the “Goat” empire. You should choose Cabra, from the same team as Girl & the Goat. This spot is on the roof of The Hoxton hotel, has a fantastic view, and also serves some very good Peruvian-inspired food. The best things on this small-plates-focused menu are the ceviches (the bass with leche de tigre and the duck are standouts), a tender and spicy skewered beef heart, and the delicious fried pork shank, which is so large that you might want to consider getting it a room at the hotel.
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 since it’s so famous, 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, remember to keep your receipt so you can show it to friends and family, and/or get it framed.
Girl And The Goat is another well-known restaurant that even your dog walker will probably tell you about. Again, that person will be right. You should come here. The global small plates menu has dishes like goat empanadas, duck tongue with wontons, and a crispy pork shank that we’d eat every week - but there are so many out-of-towners here that we can’t get a table. It does book out far in advance, but if you’re eating solo or with just one other person, you can usually find a seat at the bar.
You should make sure your trip includes at least one meal at a big, sceney River North restaurant. The trendy kind with giant booths, clubby music, big menus that will knock over your wine glass, and surprisingly great food. RPM Italian meets these requirements. It’s a downtown Chicago restaurant at its best: over-the-top, a little ridiculous, and very enjoyable. And under all the scene, it also has one of our favorite pastas in the city: the housemade cavatelli with an incredibly rich pork-and-beef ragu.
Cindy’s is the spot for views of the Chicago skyline. The menu is new American, and while the food isn’t particularly memorable, it’s decent, and you’re really here to look out the windows. We suggest coming for brunch, when you can get pancakes, egg dishes, and lots of pastries. Much of it can be shared by large groups (most dishes have a “platter” option), so it’s also good if you’re traveling with a crowd.
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.
If you’ve ever wondered what eating in a wooden hallway would be like, Avec is the answer. It’s small and narrow, with a long bar and several communal tables. It also doesn’t take reservations. This may not make it sound particularly appealing, but it’s worth a trip for its fantastic food and service. The Mediterranean small plates here are consistently delicious, so order whatever sounds good to you. Just make sure the bacon-wrapped dates and the taleggio flatbread are on your table. And get a side of honey to go with the flatbread. Trust us.
Other than Top Chefs, Au Cheval, Rick Bayless, and steakhouses, Chicago is known for Alinea. This is one of the most famous restaurants in the world, and its tasting menus can cost anywhere between $200 and $400 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 molecular-gastronomy-related theatrics, like edible balloons). Dinner here feels like a once-in-a-lifetime experience, but if you need a few more years to practice your balloon-eating etiquette before trying it out, we get it.
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.
After visiting Pequod’s, then it’s time to let Chicago showcase its incredible pizza range. After all, it’s a common misconception that this city only has deep dish, and a trip to Pizzeria Bebu can disprove it. The excellent pizza at this Lincoln Park spot has a thin, perfectly chewy and bubbled crust, and delicious toppings like meatballs with vodka sauce or salami and Calabrian honey. Almost everything is made on-site, and the non-pizza items (like roasted beets with feta and pistachio) are just as good.
Chicago has lots of taquerias, and Traspasada in West Town is our favorite late night spot. It’s a small, cash only counter operation with around 15 stools, and it serves great tacos - particularly the chorizo and al pastor. One of the best things about this place is that it’s open late (until 1am during the week and 3:30am Friday and Saturday nights). In other words, this is a good spot to sneak in that fourth meal everyone needs to do a city right.
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. So this is a must-stop. But a trip here can be confusing, since there are tons of people in multiple lines. There’s another restaurant inside the space called Barnelli’s - just ignore it and focus on staying in line for Portillo’s Hot Dogs. 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 native already.
MingHin is our favorite place in the city for dim sum, for a few reasons: the food is consistently good, you can almost always walk in and get a table, and the Chinatown location is open from 8am-2am every single day of the year. So if you’re in Chicago over the holidays and have a midnight craving for BBQ pork, sesame balls, and a salted yolk bun, this is where you should go. Follow it up with a visit to one of the karaoke bars in the neighborhood.
Sometimes first-timers visit Chicago and expect every meal to be meat-centric and heavy. And while the food at The Publican can be both of these things (this place is known as a pork and beer hall), the menu actually has a lot of seafood and vegetable options, too. More importantly, all of it is incredibly good. Plus, nowhere else in the city can you eat barbecued carrots, oysters, and porchetta while sitting at a giant wooden communal table like you’re in the Middle Ages.
The Purple Pig is located just off Michigan Avenue, so it’s convenient to whatever Disney store/Tiffany’s/Nutella Cafe shopping you’ve been doing. But unlike a lot of other restaurants in touristy spots, it doesn’t serve terrible food. The Mediterranean menu is long, with quality dishes ranging from crispy pigs’ ears to a giant confit turkey leg. Since they don’t take reservations, you might have to wait - but it shouldn’t take too long. You’ll be back at the Navy Pier Build-A-Bear in no time.