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The First Timer’s Guide To Eating In Chicago

PHOTO: Christina Slaton

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.

The Spots

Monteverde

West Loop
1020 W Madison St
8.9
MAP

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.

8.5
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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.

Au Cheval

West Loop
800 W Randolph St
9.2
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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.

8.4
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Now seems like a good time to tell you about about our restaurant overlord, Rick Bayless. He won’t let you leave Chicago unless he feeds you at least once. Frontera in River North is the crown jewel in the Rick Bayless empire (it was his first Chicago restaurant), and the food happens to be great. They serve dishes like guacamole, tacos, and moles, and everything is done exceptionally well. It’s not fancy, but not super casual either - go for a low-key lunch or dinner.

7.7
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Chicago has lots of taquerias, and Traspasada in West Town is our favorite. It’s a small, cash only counter spot with around 15 stools, and it serves excellent 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.

Maple & Ash

Gold Coast
8 W. Maple St.
8.3
MAP

Other than Top Chefs, Au Cheval, and Rick Bayless, Chicago is known for steakhouses. And we do have a lot of fantastic, traditional places, but we’re going to suggest you go to Maple and Ash in the Gold Coast. It’s over-the-top in the best way, with chandeliers, candelabras, huge velvet booths, and a $145 tasting menu called “I don’t give a fck.” If you decide you do give a fck, you can order a la carte. Either way, you’ll have a fantastic meal.

Girl & the Goat

West Loop
809 W Randolph St
8.8
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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.

Cindy's

Loop / Magnificent Mile
12 S. Michigan Ave.
7.7
MAP

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.

Avec

West Loop
615 W Randolph St
8.6
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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.

Alinea

Lincoln Park
1723 N Halsted St
9.5
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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 $300 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 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.

Roister

Fulton Market / West Loop
951 W Fulton Market
9.1
MAP

If you didn’t cash out your 401k before coming to Chicago, and you can’t afford Alinea, don’t worry. Roister is from the same team, but it’s more casual and less expensive. (By normal standards, though, it’s still a pretty fancy restaurant.) There’s a busy open kitchen in the middle of the dining room, and the new American food is fantastic. It’s perfect for dipping your toes in the Alinea waters without making the full commitment. Make sure to order the fried chicken and crispy potatoes, and get a foie gras candy bar to go.

Pequod's Pizzeria

Lincoln Park
2207 N. Clybourn Ave.
8.6
MAP

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.

Portillo's

River North
100 W. Ontario St.
8.4
MAP

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.

8.6
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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.

8.3
MAP

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.

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