BY: Alyssa Schwartz

When it comes to food and drink, the word “interesting” is usually the equivalent of saying a girl’s got a good personality. But with flavours rooted in the familiar, Chicago kitchens and bars manage to hit that elusive sweet spot between innovation and flat-out yum.

Whether you’re talking about one of North America’s most vibrant craft cocktail cultures, diners that extend comfort food into thrilling new territory, or a fine dining scene that will forever change your stuffy notions of what “fine dining” means, it’s one of the most exciting places to eat and drink right now. Here are some must-tries.

Violet Hour

In true speakeasy style, you’d never spot this place from outside. But while most underground booze joints hide down alleyways and nondescript entryways, you’ll know Violet Hour for the massive mural of a naked man drinking a martini. Inside, the bar is cavernous, dark, and dramatic. 1520 N Damen Ave


It’s the little touches that escalate Scofflaw from hipster bar to the kind of place you wish was your local – gratis cocktail “amuses bouche” (a fresh mix of Wisconsin Death’s Door gin, ginger, lemon and Peychaud’s bitters when we visited), late-night chocolate chip cookies, and events like a monthly bazaar and fan fiction nights, where the bartenders craft drinks to match a cocktail-focused book. The compact drinks menu is gin-focused and Scofflaw Old Tom Gin punch – featuring the bar’s house gin, distilled in Chicago’s North Shore – is the standout. 3201 W Armitage Avenue


Some places sneak up on you. Trenchermen, which has curiously managed to evade the hype amongst food tourists, is one of those. I came for mixologist Tona Palomino’s excellent cocktails (Pink at Night, with mescal, yuzu, ginger and grenadine, might have the hue of a girl drink but it sure doesn’t taste like one) and instantly regretted not being able to stick around for dinner. I consoled myself with perfect bar snacks, specifically the pickle tots: homemade tater tots spiked with chopped bread and butter pickles, they come with smoky bresaola-style chicken breast (think cold cuts) and tangy red onion dip. 2039 W North Ave


How do you not love a meal that starts with a tangle of twigs and smoky leaves – that’s right, it’s a campfire delivered right to your table – holding exotic bites like jackfruit and a gougere filled with fava beans? Though the menu, mostly just a list of ingredients for each course, yields minimal detail of what to expect, you already know you’re in for a trip. Just go with it. Kampachi, a Hawaiian fish related to yellowtail, is like a salad roll – only bound in ginger ice – and platings are so exquisitely beautiful it breaks your heart just a little to take a bite. 652 West Randolph St.

Au Cheval

087.JPGObviously, you’re going for the burger. Bon Appetit called it the best in the U.S. and the folks at Grace told me I couldn’t go home without sampling it, ideally topped with bacon and egg (they also cautioned me that the single is actually a double patty and double means triple. Consider yourself warned).  But chef-owner Brendan Sodikoff, who has worked under Alain Ducasse and at Thomas Keller’s French Laundry, carves out his niche at the intersection of high and low. Think a fried house-made bologna sandwich and foie gras terrine with strawberry jam, which, well, how do you not want to try that? The foie is flecked with shards of salt, strawberry jam so think and chunky enough to hold a spoon upright, along with bottomless, thick slices of toasted brioche. It’s a carnivore’s riff on good ol’ PB&J. Brilliance. 800 W Randolph St.

The Publican

 Loud, boisterous and fun – a beer hall that’s as much about the eating as it is the dozens of rare and craft brews on tap (ask your server to guide pairings to your meal order). Served family-style, The Publican’s dishes are satisfying and nostalgic but utterly fresh. Roasted Guinea hen with lentils, dates, celery and pomegranate tasted like something my bubbie would make – if she cooked with things like lentils, dates and pomegranate. 837 W Fulton Market

Little Goat

If you were to dream up a menu of perfect stoner food, this would be it. French toast made from sweet onion brioche and a baked-in egg, topped with fried chicken and BBQ maple syrup, or the fried pickle sandwich, a play on the gyro with fried pickles, hummus, hot banana peppers, goat cheese and tzatziki on house-made naan – easily the most fun veg sandwich I’ve ever seen – alongside diner classics like a perfect patty melt. Lines can be insane – an hour and a half or more on weekends – but grab a Little Goat, the signature latte made from goat milk (don’t balk), from the adjoining bakery/coffee shop and settle in. 820 West Randolph St.


Whatever notion you have of accessible dining – check it at the door. Or more accurately, lose it somewhere down the dark hall the bridges the outside world from Alinea’s Alice in Wonderland. Grant Achatz’s landmark restaurant is the Cirque de Soleil of dining – 20 mind-bending courses that sometimes require eating instructions and don’t always resemble food. Service is deliciously irreverent: When my server sets down a silicon tablecloth for dessert, he informs me it’s made from the skin of baby seals (it’s not). Tickets run $300 a head including tax and mandatory tip (wine pairings will run you another $150-250 more), but this is art, people. 1723 North Halsted

If you go:

Plan your trip: There’s more to do in Chicago than eat (we hear). Get all your trip planning details at

Stay: The Intercontinental Chicago was built as an urban country club of sorts – just prior to the 1929 stock market crash. Save some time to poke around the gorgeously-restored ballrooms and King Arthur Court.

Alyssa Schwartz is a Toronto-based travel and food writer. Find her on Twitter @alyssaschwartz.

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