1639 S. Wabash Ave., South Loop
Acadia's 10-course prix fixe menu, which includes two cocktails that are mixed table-side, earned it a Michelin star. But if you don’t have the time (or budget) for the full experience, go just to sit at the bar and order the burger, which is served with bacon onion jam, gruyere, and taleggio mornay. Though it's best reserved for exceptionally special events, their private dining room has space for 20.
1664 N. Ada St., West Town
The kitchen at Ada Street (formerly held by Zoe Schor, who is kind of a local legend for having the ingenuity to serve baby octopus with buffalo sauce and potato salad) is now run by young Chicago South Side native, Joanna Stachon, who has been with the restaurant since its early days in 2012. The menu at this hidden gem (it's quite literally hidden near a Home Depot in an unmarked building) remains exciting: gnocchi with maple bacon, steak tartare with fried capers and egg yolk, PB&J bread pudding. In the summer, they open up a garage door in the back of the building to an open-air astroturf patio; head to the back to play a game of ping pong while you wait for your meal. The private dining room here is legendary, too—tucked away near the entrance to the main dining room, it's a popular pick for the film and music crowd.
1829 W. Chicago Ave., West Town
This West Town gem was recommended by a goop friend for the freshest sushi in town. The Japanese dishes here—uni shooters, sashimi, nigiri—are all authentically modern, a testament to Executive Chef Frederick Despres.
807 W. Webster Ave., Lincoln Park
This beloved neighborhood haunt was recommended to us by a goop pal who swears it's one of the best family-friendly meals in town. The menu is packed with tasty dishes that are just simple enough to accommodate a kid’s palate. The roasted chicken in particular seems to net the most acclaim from diners both big and small.
1 W. Washington St., The Loop
Atwood's airy open dining room means that every seat—be it bar, booth, or window—is the best seat in the house. It's the kind of reliable place that covers all its bases by serving a great omelet at breakfast, quickie but filling lunch, and a solid seafood or steak dinner at night. The private mezzanine area seats up to 30, making it particularly well-suited for business lunches.
800 W. Randolph St., West Loop
Exposed brick, leather banquettes, and mood lighting make this the ideal date spot—whether it’s of the romantic or friendly variety. They don’t take reservations, so we suggest cozying up at the bar for a classic burger (many say it’s the best in town) and a cold beer (there are tons of domestic and international options). The brunch shouldn’t be missed—the fried house-made bologna sandwich with a side of hashbrowns is the restaurant’s most popular order.
615 W. Randolph St., West Loop
Avec is one of Chicago's enduring food destinations. It boasts a sleek all-wood interior, and rows of communal tables that aren't exactly comfortable, but do the job (particularly because long lines dictate that you shouldn't exactly linger). It’s technically a wine bar, so there’s an extensive wine list in addition to a selection of beers and cocktails. Food-wise, the menu is broken up into shareable plates that range from charred octopus to stuffed dates, and large plates like confit chicken paella and whole roasted fish.
1633 N. Halsted St., Lincoln Park
Balena is the second restaurant the team behind The Bristol and Formento's, and it manages to capture the same sophisticated but comfortable vibe as the former, with tall ceilings, rustic furnishings, and some seriously cool firefly-like light fixtures. The menu here is straight-up Italian, filled with classic dishes like a potato gnocchi in a mushroom sauce, a fennel sausage and onion pizza, and a classic roasted chicken with romesco and walnut parmesan. The private room has its own bar that's decorated with back-lit wine bottles for a cool stained-glass effect.
218 W. Kinzie St., River North
Like most establishments on Brendan Sodikoff’s roster (Au Cheval, Gilt Bar), the décor at this River North steakhouse is old time-y and darkly romantic (tufted leather booths, hard-wood floors, vintage mirrors) with a dinner offering that clearly values tradition over pomp: meatloaf, crisp wedge salad, and really really good steak frites. Wash it all down with something from the classics-minded cocktail list (regulars tend to go for the Dark & Stormy).
1531 N. Damen Ave., Wicker Park
Unlike so many of the city’s more popular watering holes, this indoor-outdoor Tex-Mex spot is bright, airy, and massive in size. It’s part of One Off Hospitality Group (Dove’s Luncheonette, Avec) and as evidenced by the deep tequila/beer/cocktail list and 2am closing time, values a good time above all. To balance out the copious amounts of booze, order tacos and lots of guacamole from the walk-up window—it's usually faster than waiter service.
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