Hidden Chicago: How to Visit Like a Local

Image via Complex Original

Location: 1227 West 18th St.

Dusek’s is a gastropub in the Pilsen neighborhood of Chicago that blends small plates (hello beef fat fries and braised pork shank) with 24 beers on tap—enough to keep you busy for your entire trip—but don’t forget to visit the retro-looking Punch House downstairs for a bowl of homemade champagne.

Location: 1220 North State Pkwy

Good luck spotting this Gold Coast piano bar from the street—the Zebra Lounge is built into the first floor of a historical apartment building. But inside, things get loud, and we’re not just talking about the zebra print décor. This cozy saloon specializes in the kind of old-school hits people like to shout at the top of their lungs. Consider it a vacation exercise routine.

Location: 2430 North Cannon Dr.

Local chefs pick up some of their freshest ingredients from over 70 vendors at this year-round farmers market on Saturdays (you can find it inside the Peggy Notebaert Nature Museum in the winter). Pick up a sustainably sourced snack or a bag of produce and you’ll feel better about devouring a calorie bomb of a dinner later.  

Location: 1804 North Damen Ave.; 1753 North Damen Ave.

In Bucktown, a neighborhood known for it’s shopping, you'll find some of the best men’s boutiques in the Midwest on Damen Avenue, including Apartment Number 9 (home to brands like Band of Outsiders and A.P.C) and RSVP Gallery—a subterranean and neon-lit lifestyle shop that blends art, streetwear, and high fashion. 

Location: 1655 North Sedgwick St.​

This divey-looking joint tucked away in Old Town has zero scene—as in, there’s no need to rock the new clothes that you just picked up from Damen Avenue. Sweatpants are fine, and maybe even necessary, because once your lips hit a Twin Anchors rack of ribs smothered in zesty BBQ and paired with a loaded baked potato or onion rings, you won’t want to leave. 

Location: 2548 North Halsted

Kingston Mines features live music from local artists on two separate stages, seven nights a week. Plus, the cover is minimal. You’ll want to catch regular blues musician Joanna Connor for an amazing guitar solo, for starters. Kingston is also open late (until 4 a.m. most nights, or 5 a.m. on Saturdays) so if you want to really explore Chicago like a local, pop in after the other bars close. 

Location: 1501 North Kingsbury St.​

When comedy club The Second City is sold out (or swarming with out-of-towners), iO Chicago is a safer—and equally hilarious—bet for improv and sketch comedy shows. Notable alumni include Tina Fey, Amy Poehler, Chris Farley, and pretty much everyone else who made it big on Saturday Night Live.

Location: 1520 North Damen​

There is no sign directing you to enter this candle-lit speakeasy in Wicker Park, and you’ll be asked to refrain from using your phone inside The Violet Hour. But there’s plenty to talk about at this cozy retreat—like the assortment of bitters and pristinely cut ice that accompany the various cocktails.

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