The Chicago Greatest Hits List

Our guide to the 26 quintessential restaurants that make Chicago dining what it is.

Welcome to The Infatuation’s Chicago Greatest Hits List.

Obviously you’re familiar with the concept of a “greatest hits” album, but to be clear, this is not just a list of our highest-rated spots. This guide is a carefully selected collection of the places we think every Chicagoan should try at least once - and the restaurants you should prioritize if you’re new to town.

Just like you wouldn’t introduce someone to The Eagles without starting with “Hotel California,” or to The Steve Miller band by playing them that one song they didn’t put on a greatest hits album, we wouldn’t send someone to a new Chicago hotspot without sending them to one of these restaurants first. You shouldn’t either.

If you are looking for what’s new, check out our Hit List, a guide to the brand new, recently-opened restaurants worth your time.

Added 2/2020: Pizzeria Bebu, Daisies, Ras Dashen

The Spots

This is one of the most famous restaurants in Chicago. And thanks to a documentary you vaguely remember seeing, if you have a fancy-restaurant bucket list, Alinea is probably on it. Of course, fame and documentaries don’t necessarily mean a place is worth your time (or in this case, several hundred dollars of your money) - but Alinea deserves its spot at the top of this list. Not only is the food delicious, but a meal here is also guaranteed to be bonkers, with theatrics (like fog machines) and molecular gastronomy (like edible balloons) you won’t easily forget. If you’re going to be late on your car payment because of a meal, make it this one.

The burger here is so legendary, there’s practically an Au Cheval shuttle from O’Hare for people visiting Chicago. And it’s not overhyped - with its grilled double patty, thick-cut bacon, and buttery bun, it’s still the best burger in the city. But it’s also not the only thing worth ordering at this restaurant. The bone marrow with oxtail marmalade is outstanding, the chilaquiles are fantastic, and the glazed chicken wings should be on your table, too. Despite the high likelihood that you’ll have a three-hour wait, this is a place you need to visit at least once.

A few things set Chicago apart from other major cities. One, living here is affordable enough that having a roommate when you’re 28 years old is a choice. Two, we have more former Top Chef contestants per capita than any other city. Monteverde is a Top Chef spot, and it also happens to have the best Italian food around. Every dish here is fantastic, from the housemade pastas like cacio e pepe and tortelli di zucca, to the ragu alla Napoletana (with perfectly cooked pork shank, sausage, meatballs, and fusilli), which is one of the most delicious plates of food we’ve ever eaten. Come here on a date, come here with a group, or come here by yourself and order every single pasta you can fit on the table in front of you. The point is, there’s no scenario in which this restaurant isn’t a great choice.

This place (which happens to be another Top Chef spot) is deceptively unassuming - it’s on a pretty much deserted street in Avondale, with only a “P” above the door for a sign, and an equally understated interior. The Korean/American food here is always changing, but you can expect dishes like ddukbokki with pork sofrito, perfectly fried japchae tempura, and a seafood bibimbap that sounds simple but tastes anything but. Parachute also has the kind of service that will remind you why Midwesterners have a reputation for being very nice. If you’re looking for proof that Chicago has more to offer than steaks and deep dish, this is a great place to start.

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You can’t have a Chicago Greatest Hits list without deep dish pizza, and Pequod’s serves the city’s best. Unlike traditional Chicago-style deep dish, which has sauce on top, Pequod’s does pan-style pies, with a spicy sauce underneath the toppings and a thick and airy crust. What really sets the pies here apart, though, is the “caramelized” crust, a.k.a. the burnt edges of crispy cheese around the edge. The original is in Morton Grove, but we prefer the Lincoln Park location - it’s basically a sports bar, always crowded, and perfect for a group. Order the pepperoni.

Lou Malnati’s pizza is the epitome of classic Chicago deep dish (the kind that New Yorkers love to hate), and is our favorite of its type. It has a buttery and flaky crust, a ton of cheese, and lots of sauce on the top - so it’s a gooey mess, and will require the use of a fork and knife. This is probably why it’s an abomination to the rest of the world, but we’re really glad Chicago isn’t closed-minded, because this sh*t is delicious.

5 Rabanitos has everything you want from a casual Mexican restaurant in Chicago. There’s a long menu of delicious, affordable food (ranging from $3 - $18, with most dishes being around $10), and we have yet to find something disappointing on it. We especially like the tacos, the ahogada torta, the huaraches, and the carne asada. Make sure to come with a bunch of friends so you can share as many things as possible.

Girl & the Goat is so famous that you may be wondering if at this point, it’s just old news and/or a tourist trap. But it’s not either of those things. The wide-ranging small plates menu changes often, but there are always delicious staples like the pig face, various goat-based items (e.g. empanadas), and a must-order pork shank. There’s a reason this place is still hard to get into nine years after it opened.

We take every possible opportunity to tell people to eat at Giant in Logan Square. On the surface, its new American menu looks like every other one you might have encountered over the past decade - but this place somehow manages to make a dish like broccoli and cheese a must-order. (You also need the crab salad with homemade waffle fries, and a pasta like the tagliatelle with crab and uni butter.) It’s small, so you might have trouble getting in - but in the summer there’s a hidden back patio that adds more space, and the first-come-first-served chef’s table is worth taking your chances on.

Between the fantastic Ethiopian food and incredibly friendly service, it’s impossible to leave Ras Dashen in a bad mood. And in a city where people can go months without seeing the sun, this is important information to have. Not only is the food across the board outstanding, but it’s the kind of place where you’ll see the owner cooking in the kitchen, and your server will be excited to tell you their favorite dishes on the menu. That’s how we discovered the shimbera asa wat (chickpea dough in a spicy berbere stew), and the misser salata (a refreshing lentil salad) and our lives are better for it. Plus, their spongy injera bread (made fresh daily) is the best we’ve had in Chicago.

There are approximately 349,8755 steakhouses in this city, many of which are perfectly fine. But before you start working your way through them all, there’s a classic you have to hit first: Gibsons in the Gold Coast. It has everything you want from an old-school Chicago spot - celebrity photos on the wall when you walk in, fantastic steaks presented tableside, and six-pound desserts (literally) to round everything out. On any given night, the dining room here will be filled with businesspeople, tourists in sweatshirts, and couples getting engaged. Everyone seems like they’re having a great time (because they are), and this place is as good for people-watching as it is for food.

If your goal is to eat the best piece of steak you can possibly find, go to Bavette’s. The bone-in ribeye here is perfectly cooked, and might actually ruin you for all other steaks. That said, some of the best dishes here (like the short rib stroganoff, bone marrow, and fried chicken) aren’t steak at all. Add in the dark speakeasy environment and the fantastic complimentary bread (yes, it’s really that good), and it’s no mystery why you need to book months in advance if you don’t want to eat here on a Monday at 5:30pm.

Out-of-towners planning trips to Chicago may already know the importance of making reservations at Bavette’s, or heading straight to Au Cheval with all their luggage. But Chicagoans know they can just go to Gilt Bar. It’s owned by the same team, but it’s been around longer, and is essentially a shortcut to some of the best things on both other spots’ menus. It has a great double cut coal-fired ribeye, and an exact replica of the Au Cheval cheeseburger. It also has the same kind of dimly-lit speakeasy environment you’ll find at all its sister spots, and you can almost always just walk in and get a table. So basically, this restaurant is where you’ll find us.

photo credit: Garrett Sweet

Oriole review image


$$$$(312) 877-5339

Oriole is definitely not your average Tuesday night dinner spot - it’s an expensive tasting menu restaurant that does 13 courses for $215. But the environment (which you enter through a non-working freight elevator in an alley in the West Loop) isn’t stuffy at all. Servers pay just the right amount of attention while presenting you with some of the best dishes you’ll ever eat - like a truffle pasta that will finally convince you that truffles aren’t just a scam - and at no point during dinner will you wonder if the high price was worth it. Other than Alinea, this is our favorite fancy dinner experience in the city.

If you’ve read this far, you know that Chicago isn’t suffering from a lack of great tasting menu spots. And the nine-course, $160 meal at Schwa is another one. But this place probably isn’t what you immediately picture when someone says “tasting menu.” It feels more like a house party than an upscale dinner - there’s a soundtrack of loud rock and rap music, and at some point you’ll probably hear some cursing from the chefs (maybe when you walk into the kitchen to get to the bathroom). The self-described “F*cking Mind Blowing Menu,” which has some molecular gastronomy touches, is excellent, but has no wine pairing option, since this place is BYOB.

On the surface, The Publican seems like it’s all about pork and beer (maybe because of the sign that’s an outline of a pig and a keg). But the menu actually has as much space, if not more, devoted to seafood and vegetable dishes, not to mention some excellent desserts. So while you should definitely order the porchetta and pork rinds here, don’t overlook the barbecue carrots, or dishes like skate wing pasta. Come for a large group meal, which you can eat at the giant wooden communal table that seats about 5000 people. The whole place feels a little like a medieval European feast, just with fewer swords and (we assume) more oysters.

When all else fails, go to Avec. The food at this Mediterranean small-plates place is always going to make you happy - particularly staple dishes like the bacon-stuffed, chorizo-wrapped dates, and the taleggio flatbread. The dining room feels like a wooden shoebox, so you’ll probably be elbow to elbow with strangers, but this place is really best experienced when you come alone or with one other person and eat at the bar. We encourage you to eat at Avec every now and then to remind yourself how reliably outstanding it is.

Frontera has been in River North for over 30 years, since way before the neighborhood became ground zero for party trolleys and Rick Bayless (who runs this place) earned his eighth key to the city. The constantly-changing menu is full of fantastic things like duck manchamanteles (made with ancho, peanuts, almonds, and pineapple), carne asada with plantains and black beans, and enchiladas. Plus, the moles (a specialty here) are complex and flavorful, and the meat is always perfectly cooked. It’s perfect for a group meal or casual-ish date night in the neighborhood.

This neighborhood spot is extremely casual, and the service is brusque, but the huge portions of reasonably-priced, Greek food will make you forget all about that. The must-order dish (and reason we send everyone here) is the Kalamata chicken. It’s roasted and served with chicken-jus-soaked fries that we would name our children after if we weren’t worried “chicken jus fries” was about to become too popular as a baby name. They don’t serve alcohol here, but you can bring it over from the bar next door.

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. And just in case you don’t get the point, Daisies decorated the bright space with large drawings of produce. Basically, it’s exactly the kind of farm-to-table place that makes us glad we’re in a city surrounded by actual farms.

RPM Italian is a quintessential River North restaurant, and basically the kind of place that you can only find in Chicago. First of all, it’s owned by E! Reality stars. Secondly, it has trendy music, big booths that can fit eight of your closest friends, and a space so large it will remind you that our city blocks are about three times the length of New York’s. Most importantly, though, the Italian food is delicious.

Over the past few years, Logan Square has filled up with popular restaurants. But before them all, there was Lula Cafe. It opened in 1999, and it’s been doing farm-to-table food since before that was even a thing. These days, it’s both a casual neighborhood restaurant and a destination-worthy spot for breakfast, lunch, or dinner. The menu is new American, and you can get everything from a smoked trout scramble to creative dishes that sound terrible (like cinnamon and feta pasta or squash ice cream) but are really delicious. We promise.

Calumet is a fish smokehouse that has been around since 1948, and it’s just a shack on the 95th Street Bridge over the Calumet River, wedged between Lake Michigan and the Chicago Skyway. They smoke shrimp, whitefish, salmon, trout, catfish, and a lot more in their little wood smoker out back using actual wood. And if you haven’t been here yet, that needs to change immediately. Just know there’s no place to sit, so come in the summer when you can sit outside, or plan on eating in your car.

There’s a lot we can say about Chicago hot dogs and Italian beefs, and many places we can endorse for them. But only Portillo’s is a Greatest Hit. Some people might complain that it’s “gone commercial” (and sure, there are locations in six other states), but that doesn’t change the fact that it started here, and it’s as good as it always was. Your Italian beef should absolutely be ordered with a Chicago-style hot dog as a chaser - and a piece of chocolate cake, too, for good measure. If you immediately decide you need it at your wedding, you’ll be in good company.

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