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Al's Italian Beef
If you're not from Chicago, you might not have even heard of an Italian Beef sandwich. And that's a damn shame, because it's friggin' glorious, when done right.

Here in Chicago we just call it a "beef", and Al's does better than anybody. Get your beef with sweet and hot peppers, juicy (this means they dip the whole thing in juice after assembly, an essential step).

If you want to eat like a Chicago municipal worker, order an Italian Combo, which means they nestle a whole Italian sausage in amongst the beef. You'll be changed by this, if you live to tell of it.

If you're going for full authenticity, trek over to the Al's Beef location on Taylor Street in Little Italy. It's the original, and it's even better.
Good For: Cops, Sturdy Folk, Food Comas
Al's Italian Beef
avec
One-off Hospitality's communal eating concept features delicious mediterranean-inspired small plates (chorizo-stuffed bacon-wrapped dates in spicy marinara are the signature dish), a fantastic wine list, and friendly, impeccable service in a cozy setting that looks like a sauna, in a good way.

You'll be seated very close to other patrons, and they will likely be attractive and well-dressed. If you're going to make friends, they might as well be beautiful and well-fed, right? See and be seen, and enjoy a unique and fantastic dining experience.
Good For: Lunch, Dinner, Drinks, Vegetarian, Making Friends
avec
Goddess and the Baker
If you're looking to Instagram your breakfast and make all of your friends back home jealous, Goddess and the Baker is the place to go. With items like "liquid gold glitter lattes" and "rainbow cake" on the menu, it's hard to argue with their "artisanal" label.

But don't let the trendiness put you off; Goddess and the Baker's food is just as good as their ambiance, and they have lots of vegan and gluten-free options as well!
Good For: Breakfast, Lunch, Coffee, Instagram, Gluten-Free, Vegan
Goddess and the Baker
Kuma's Corner
If you like your burger served with a side of unbridled anger, head over to Kuma's. Zero effs given at Kuma's, and none required. They serve up baller burgers ("Plague Bringer" is my favorite.), with aggressive brews and bourbons to wash them down, the combination of which turns out to be the antidote for fussy-food-itis.
Good For: Metalheads, Burger Lovers, Adam Wathan
Kuma's Corner
Little Goat Diner
Stephanie Izard really likes goats, and has named a whole series of Chicago restaurants after them. This one is the most approachable, and you can actually get a table less than a month in advance.

LGD features diner favorites on its massive menu, but nearly everything is done much better than you're used to, with the help of a distinct Korean influence. It's open early, and open late, and they have a small but well-curated list of beers and cocktails, so it's basically everything you need if you can't figure out where else to go eat while you're here.
Good For: Breakfast, Lunch, Brunch, After Hours, Hair of the Dog
Little Goat Diner
Manny's Deli
A proper Jewish deli in the South Loop. Go here and get a Reuben or a Pastrami sandwich. The sandwich will be enough to feed two hungry adults, and yet you'll still find room for the latke and a bowl of matzo ball soup. Sublime.
Good For: Sturdy Eaters, Kosher Keepers
Manny's Deli
Monteverde
The best Italian going in Chicago right now, and that's saying a lot. Ridiculously fresh pastas are handmade daily. Fantastic and creative cocktails, and a beautiful interior round out the experience. Highly recommended.
Good For: Groups, Dates, Foodies
Monteverde
Pequod's Pizza
Disclaimer: Pequod's is nowhere near the loop. It's in Lincoln Park. But if you have time to trek up there, it's the best deep dish pizza in Chicago, a fact disputed by no one.

If you want stay closer to downtown, Try Lou Malnati's. Stay away from Pizzeria Uno or Pizzeria Due, unless you like being treated like a clueless tourist.
Good For: Dinner, Pizza Lovers, Humans
Pequod's Pizza
Signature Room at the 95th
A chill alternative to the Sears (Willis) Tower Skydeck, the Signature Room offers amazing views near the top of the John Hancock building.

Enjoy dinner (the food is solid) at the Signature Room proper, or head up to the Lounge on the 96th floor for a cocktail or a snack. A uniquely Chicago experience.
Good For: Romance, Sunsets, Instagram
Signature Room at the 95th
The Publican
"Beer, pork, and oysters" is the description on their website. That's spot on, but Publican is so much more than that.

The European-style beer hall that spawned a culinary empire. Rustic, hearty fare with large-format beers you've never heard of, eclectic seafood (not all of it raw), and amazing house-made charcuterie and bread, each of which has spawned its own separate store (Publican Quality Meats and Publican Quality Bread, respectively). Their delicious vegetables dishes are also not to be overlooked.

Everything great about eating and drinking in Chicago under one roof. Just go.
Good For: Beer Lovers, Raw Bar, Bigger Groups
The Publican
Wildberry Pancakes and Cafe
If you're a believer that breakfast is the most important meal of the day (or maybe you just have a hankering for pancakes), then a trip to Wildberry Cafe is a must.

Note: They maintain a waitlist via Yelp, so make sure to check that out before you head over!
Good For: Pancakes, Omelets, All Breakfast Foods
Wildberry Pancakes and Cafe