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Welcome to Chicago, Illinois

Some cities have a theater district, but Chicago’s theater scene is city-wide, with hundreds of small neighborhood theaters in storefronts and churches, grand old Art Deco palaces, avant-garde venues, and sleek, modern stages. Chicago, nicknamed the Second City, is pulsing with performance art. From experimental dance to “footwork,” opera to hip hop, old-time jazz joints to underground indie rock clubs, it’s impossible to get bored in this town. The food’s not too shabby either! To give you an insider’s look at Chi-Town, we asked the locals what to do when you visit. Here are a few favorites:

Start at the Top

Views of the Chicago skyline from a local park
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Spend an afternoon peeking into open studios at the city’s oldest fine arts colony, the Fine Arts Building. Just a block from the Art Institute and across the street from gorgeous Grant Park, this 1885 former Studebaker Company Art Nouveau structure is itself a work of art. You’ll find it all: painters’ studios, record stores, yoga studios, opera rehearsal rooms, violin makers… Locals recommend riding the building’s original, manually-operated lifts to the 10th floor penthouse and winding their way down, “stopping wherever interests you.”

Local at the Fine Arts Building in Chicago, Illinois
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Outperforming

For the community theater experience, locals love Chicago Danztheatre Ensemble, which presents “performance with a purpose” in Ebenezer Lutheran Church in the historic Swedish neighborhood of Andersonville. For dance with a side of ooh-la-la, burlesque—and similarly semi-clad “boylesque”—has made a comeback in Chicago. Look for it at the “Naughty Little Cabaret” at The Original Mother's, an old-school single’s bar with a subterranean dancefloor. For jazz, poetry and a Saturday afternoon “live magazine,” head for the beloved Green Mill Lounge, an ancient Uptown institution. Insider’s tip: Go on Sunday nights, when Marc Smith—the founder of the Slam Poetry movement—leads a slam. When his name is mentioned, the crowd shouts, “So What!” Why? Because it “silences the ego, to get at the true art.” So join in and help an artist out.

Jazz singers in Chicago lounge
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Comfort Food Classics

There’s something to be said for doing one thing and doing it well. Aptly named, Cheesie’s is a grilled cheese shop and only a grilled cheese shop. Open until 5am and serving a dozen takes on the beloved grilled cheese sandwich, this place feels like it was made for brisk days or ANY after-hours nights. Satisfy your hankering with the “Frenchie,” which is American cheese, mozzarella cheese, cheddar cheese sauce, classic thick-cut French fries, bacon and chives on sourdough bread and, as if that weren’t enough, served with sour cream dipping sauce. Locals say that everything at Cheesie’s is packed with Midwestern flavor, which we’re told translates to “not concerned with carbs if things taste good.” For a Chicagoland classic, hit Portillo's and grab a Maxwell Street-style, char-grilled Polish sausage with grilled onions and yellow mustard. Wash it down a chocolate cake shake—yes, a slice of cake blended into a thick chocolate shake—for a thick, frothy glass of happiness.

Chicago-style hot dog
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Sophisticated Eats

Midwestern grub might be known for an abundance of rib-sticking meat and cheese. The Near West Side’s Girl and The Goat has plenty of duck tongue and pork face and lamb ribs. But despite its nose-to-tail reputation, the food here is light and nuanced and shares a menu with elegant veggie sides like roasted cauliflower with pickled peppers, pine nuts and mint or chickpea fritter chaat—an Indian savory snack—with carrot hummus. Sister restaurant Little Goat has the same multicultural mix of influences but with a diner feel and an emphasis on comfort foods like a sloppy Joe made with goat meat or home fries with pork belly, cilantro, and fish sauce vinaigrette. Locals come for the “Southern comfort” shrimp and grits and killer pork belly benedict. And don’t forget the vino. For the good stuff, head over to Webster's Wine Bar, where there’s a 400-bottle list, outdoor seating, and a perfect-for-wine Mediterranean menu of steak tartar, mussels and frites, charcuterie and cheese.

Webster's Wine Bar
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Dancing in the Streets

For a distinctly Chicago cultural phenomena, check out some footwork, which locals describe as “the fastest dance you've ever seen.” This freestyle form of street performance “looks like it’s choreographed, but it’s not.” To catch it outside of its natural habitat—the streets—head to Primary, a club where you can dance all night alongside footwork masters.

Footwork in Chicago, Illinois
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Hear It Here First

Chicago is a thrilling music town, especially if you want to small bands and lesser-known artists before they’ve made a name for themselves on the national scene. On the northside, Lincoln Hall hosts “up and comers” in a century-old former movie theater where the FBI famously took aim at notorious mobster John Dillinger in 1934. The 500-person venue was started by the former owners of Schubas, a venerated venue in an old Schlitz beer factory, where big name bands like Dave Matthews, Modest Mouse, Feist, and My Morning Jacket got their start in the city. For a kitschier night out, Emporium is a beer bar, indie music venue, and arcade in one. Shows are cheap or free, the beer list is long and varied, and the games will make you feel like a kid again.

Lincoln Hall
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Go Long

Deep in the heart of one of Chicago’s hippest neighborhoods, Logan Square, The Longman and Eagle is a gastropub, whiskey lounge (with over 400 obscure and revered bottles), and old-fashioned six-room inn for sleeping off an evening’s shenanigans. From the jaw-droppingly long whiskey list, the bar serves three dozen options at just $3 a shot. Or you go low-brow and slurp down $3 cans of Old Style, Chicago’s cheap beer of choice. Locals recommend the bacon cheeseburger, excellent Old Fashioneds, and the company: “This is a great place if you're alone and want to strike up a conversation at the bar.”

Bartender at the Longman and Eagle
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