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Chicago's South Side Story

From free-jazz jams to cheese-stuffed pretzels, Chicago’s once-industrial area gets creative.

ChicagoTaking a walk on the bright side on 18th Street in Pilsen, the epicentre, in the 1800s, of the world's second-largest Czech-populated city.

It's not out of the ordinary to sit in a dive bar on Chicago's working-class South Side and have a union tradesman buy you a stiff drink. But the bourbon and ginger that Mike Marszewski hands me contains an unexpected twist that I can't stop staring at: that neon-green maraschino cherry lurking at the bottom. "We call it a Bubbly Creek," says Marszewski, himself cradling a glass of pink Wild Blossom mead fermented exactly 70 blocks south of here. "The real Bubbly Creek is the old runoff from the former meatpacking plants up the street. It wasn't radioactive or anything, but let's just say there was some weird stuff going on in there."

Not so at Maria's Packaged Goods and Community Bar, the hopping watering hole that Marszewski runs with his brother, Ed, in Bridgeport, a neighbourhood of old brick row houses once known as Hardscrabble and populated by Irish canal workers. To get here, I take the Orange CTA line, then pass under an expressway and its six lanes of traffic and turn left at a funeral home. But despite what seems like a trek, I find the place packed with patrons poring over the 13-page drinks list, the buzz a symbol, perhaps, of the changing fortunes in this part of town. "Our joke used to be, 'Bridgeport: the Community of the Future – if the future was the Apocalypse,'" says Ed from behind his black Wayfarer glasses.

ChicagoLeft to right: Dusek's Board & Beer, in Pilsen, was named Chicago's best new restaurant by Chicago magazine earlier this year; Bruce Finkelman, Dusek's owner.

When the poet Carl Sandburg opened his 1914 poem "Chicago" with the phrase "HOG Butcher for the World," he wasn't talking about the swish northern boulevards of the Gold Coast. America's second city, running up and down the natural border of Lake Michigan, is a town divided. And the two Chicagos don't just have their own baseball teams; the polished North Side, where preppy Cubs fans flood the neighbourhood bars around Wrigley Field, has long overshadowed the working-class South Side that cheers on its White Sox by tailgating in sprawling, faceless parking lots off the Interstate Expressway, including a patch of asphalt that was once the site of Comiskey Park and the Sox's home plate. But now the neighbourhoods below Roosevelt Road, home to deep-rooted populations of immigrants and African-Americans and Latinos, are staging a cultural comeback that's giving visitors like me plenty of reasons to steer south. And, like the Marszewskis, instead of tearing history down and starting afresh, South Siders are sprucing up the neglected but sturdy bones of their communities.

On this Friday night, the Marszewski brothers are telling me they took over Kaplan's, a traditional Chicago "slashie" (half bottle shop, half watering hole) from their mother, Maria, in 2010. They repurposed its Art Deco carved-wood beer cooler as a space divider, installed beer-bottle chandeliers sculpted by Ed's wife, Rachel, and rechristened the spot. "All the locals had been calling it Maria's for years anyway," says Ed, who owns an art gallery two blocks away called Co-Prosperity Sphere. I slug back my libation – Old Grand-Dad 100 Proof bourbon, blood-orange bitters rinse and ginger beer made by nearby Filbert's – and bite down on the radioactive cherry. Then our dinner from the Pleasant House Bakery next door arrives. Delivered by a dude with tattoos, our flaky pot pies are stuffed not with meat and potatoes but with mushrooms and kale.

ChicagoLeft to Right: Musician and University of Chicago's Arts Incubator artist-in-residence David Boykin; tending to the plants at the Plant is a growing concern for Rebecca MacDonald, an environmental sustainability student.

South of Maria's – a few blocks from the stadium where the White Sox play – I descend deep into the basement of a four-storey former meatpacking facility operated from 1925 until 2006 by Peer Foods. I'm on a guided tour of the Plant, a vertical urban farm and small business incubator founded by John Edel; naturally, everybody's taking photos of lettuce and Swiss chard. The Plant is home to a closed-loop aquaponics system: Resilient tilapia are farmed in tanks and their wastewater is piped across the room to provide a nutrient-rich growing medium for plants that, in turn, send clean water back to the fish.

"Think about it: This area used to be the epicentre of American industrial might," says Edel at the end of the tour, as couples with young children line up to buy fresh basil and mushrooms and salad greens displayed on a small wooden table. Somehow, this factory that once sent pork chops by rail to the far corners of the United States has become something more akin to a Saturday neighbourhood farmers' market: Pleasant House grows produce for its kale-and-mushroom pies on the second floor, while the Plant sends its own tilapia north to Fish Bar, Chicago's hip seafood shack. A craft brewery is coming soon – Edel's vision is to use the spent brewing grain to feed the fish. "We're trying to create jobs, sure," says Edel just before I depart with a half-dozen whole-wheat English muffins from a bakery called Peerless Bread & Jam. He's covered in a thin layer of cement dust from boring holes through a 20-centimetre-thick concrete ceiling. "But we're also aiming to give people around here some pride of place."

Maria's, ChicagoPart bar, part bottle shop, Maria's Packaged Goods and Community Bar, in Bridgeport, features a 13-page drinks list and some 475 beers.

I soon learn that even the city's legendary jazz scene – it was at Bronzeville's mixed-race Sunset Cafe that jazz greats like Benny Goodman and Louis Armstrong created the famed "Chicago Sound" – is getting an update. Over in Washington Park, a modern bandleader named David Boykin is creating a new Chicago sound with his weekly Sonic Healing Ministries jam. As I enter the Arts Incubator, until recently an abandoned 1920s-era structure on Garfield Boulevard that the University of Chicago rescued with the help of artist-cum-community activist Theaster Gates, incense hangs in the air. Boykin, sliding across the wood floor in his socks, and his Microcosmic Sound Orchestra launch into a manic freestyle jam. I'm one of the first to arrive – it's just me and a girl in a blue satin dress reading We Can't Breathe, by local African-American novelist Ronald Fair – but soon a steady stream of curious interlopers wander in from the street and we all fill plates with free chips and guacamole.

ChicagoLeft to right: In addition to Dusek's, Thalia Hall houses a refurbished concert hall and the Punch House basement lounge; Washington Park residents Shawn McNeal and Anton Campbell strike a pose.

The Arts Incubator, with its restored terracotta facade, features a big-windowed gallery space on the corner and studio space for rotating artists-in-residence, of which Boykin is one. I run into all sorts here today, from the actor Danny Glover to some more down-on-their-luck types, perhaps drawn by the free snacks. But Boykin's sound, which shifts character from sinuous to sweet and back again, eventually touches everyone. "Psychic healers, mystic travellers, march to the eastern sunrise and conjure a new reality," speaks the saxophonist Eliel Sherman Storey. A strange kid in a purple tunic and John Lennon glasses – he's been carefully sanding a collection of chicken bones for the past hour, and I decide not to pry for an explanation – stands up during one particularly frantic musical freak-out and begins twitching, like a man experiencing a religious tantrum. "That was like Armageddon and Revelations rolled into one," he whispers to me when the jam slows back down. I give him a nod back, my own little reciprocal amen.

ChicagoLeft to right: Maria Marszewski handles the register at her sons' watering hole; Mike Marszewski is the co-owner, with his brother Ed, of Maria's Packaged Goods and Community Bar.

"Look, nothing we're doing here is original," says impresario Bruce Finkelman, as we meet up the next day outside Thalia Hall in Pilsen. John Dusek built this community hall, including a theatre modelled after the Old Opera House in Prague, in 1892; at the time, Chicago was the second-largest Czech-populated city in the world. "We let the bones of the building dictate what it was going to be," says Finkelman, who purchased the structure with partner Craig Golden in 2013. We pass through Dusek's Board & Beer – one quick bite of the cheese-stuffed pretzel and I understand why Chicago magazine recently named it the city's best new restaurant – and into the newly opened concert hall. There's still scaffolding everywhere; between show dates, craftsmen are restoring the original tin proscenium and stripping down layers of wall covering to expose the original murals. "We could have thrown a coat of paint on it and left it at that, but we decided to open it as a work in progress, and take the time to do it right," says Finkelman. "It was important to us that the building act as what it was in the 1890s: a beacon of the community."

I retire to Finkelman's basement bar below Thalia Hall, a rec-roomy grotto named Punch House, to meet some North Side friends who've ventured south for a night of group-effort cocktails. Tonight's elixir is a Milk Punch – brandy, lemon, nutmeg, milk whey – whose recipe dates back more than three centuries, and we take turns ladling it from a large vintage glass bowl into our mismatched teacups. It's South Side community spirit in the most literal, old-school sense imaginable, and I'm tipsy on it soon enough.

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