Near the Hotels
Get Drinks
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
Cindy's
Stunning rooftop cocktail spot above the revamped Chicago Athletic Association on Michigan Avenue. If the weather is nice, this is hard to beat downtown.
Good For: Drinks, Fresh Air, People Watching
Cindy's
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
Milk Room
If money is no object, make a reservation at this one-of-a-kind cocktail bar, where you can drink very, VERY old booze in a ultra cozy 8-seat room.
Good For: Serious Drinkers, Expense Accounts
Milk Room
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
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