You cannot paint Chicago with a single brush. This sprawling cosmopolitan metropolis boasts fascinating neighborhoods that range from the grandeur of Downtown to the heritage of Hyde Park to the hipsterdom of Wicker Park. Our five locals each provide a distinct view of their city, but what unites them all is a sense of civic pride and a love for the diversity of Chicago’s palette.

For more on Chicago, see our city guide here.


The Homespun Revival of the South Side
Joe Flamm, 33
Celebrity Chef

Joe Flamm’s picture sits front-and-center outside Spiaggia, a Michelin-starred Italian restaurant on Chicago’s tony Gold Coast. He’s been executive chef here for nearly five years, but having finished his shift this evening, the 2018 Top Chef winner is heading for a less rarefied part of town. “People have their idea of what the South Side is,” Flamm says of the area he grew up in. “But they don’t really know it.”

Raised in blue-collar Ashburn (his mother was a police officer), Flamm knows the South Side better than most. The area was rough back then, but there were strong ties among those who lived here, and that spirit has contributed to the success of the shops, restaurants and bars that have popped up in recent years—there is little need for “Support Your Local Business” signs in these parts. “There are generations of family here,” Flamm says. “Everybody knows each other. It’s just super neighborhood-oriented like that.”

After dropping out of university, Flamm attended Chicago’s Le Cordon Bleu College of Culinary Arts, going on to work for some of the city’s brightest chefs: Art Smith at Table Fifty-Two, Stephanie Izard at Girl and the Goat, Bill Kim at BellyQ and Tony Mantuano at Spiaggia. When asked about his success, he returns to the prevailing attitudes of his home. “There’s a work ethic and grit down here,” he says. “It’s just the kind of place it is.”

In fact, Flamm adds, the South Side’s ongoing revival owes more to this roll-up-your-sleeves mentality than an influx of venture capital. “Everybody knows that if you’re trying to do something, you’ve got to go out there and get it.” Tonight, he wants to show me a couple of neighborhoods that epitomize this spirit, starting in Pilsen, whose rising fortunes can be measured by the absence of parking spaces. “You used to be able to just throw your car in the middle of the street,” Flamm says, crawling along 18th Street. “Now look at it!”

Having parked the car, we walk roads lined with workers’ cottages and Bohemian baroque buildings, along with scores of vibrant murals, part of a public-art movement jump-started in 1968 by Mario Castillo’s anti-war mural Peace (a.k.a. Metafisica)—yet another expression of the local capacity for self-renewal.

Located just below Little Italy, Pilsen has long been home to a large Mexican community—hence the surfeit of traditional family eateries like Taqueria Los ComalesCarnitas Don Pedro and 5 Rabanitos Restaurante & Taqueria. There’s a south-of-the-border flavor to the cultural scene, too, most visibly in the sprawling National Museum of Mexican Art, but also in the Día de los Muertos-themed items at the colorful Mestiza boutique.

In recent years, Pilsen’s dining options have expanded to include spots like the gastropub Dusek’s Board and Beer, situated below the 19th-century opera house Thalia Hall, now a venue for everything from hip-hop to metal. Not far from here is HaiSous Vietnamese Kitchen, with its jazzed-up street food (octopus with confit eggplant), and the brewpub Alulu, popular for its elevated bar food (poutine with pickled peppers). 

We step through the unmarked doorway of S.K.Y., chef Stephen Gillanders’ acclaimed contemporary American restaurant. “Not a lot to complain about with a leg of duck confit all glazed up,” Flamm says, digging in to one of the eatery’s signature dishes.

“The thought, even five years ago, of me eating something like this in this neighborhood would have been unfathomable.”

After a quick pint at Skylark, a popular late-night watering hole among local chefs, we head south to Bridgeport. Dubbed the “New Chinatown” for its abundance of Asian restaurants (Taipei CaféPot Sticker House), the area is also one of Chicago’s liveliest arts districts, with spaces like the Zhou B Art Center, the Co-Prosperity Sphere and the Bridgeport Art Center setting the pace.

Formerly a hardscrabble Irish community, Bridgeport’s diverse ethnic makeup is reflected in the variety of its restaurants—the Polish-Korean Kimski, for instance, which serves up pierogies alongside pork belly bowls. Adjoining this is Maria’s Packaged Goods & Community Bar, a traditional “slashie”—part liquor store, part local tavern—with a large craft beer menu. Flamm and I take a seat at the Kimski counter, where, over an order of sweet-and-spicy “Kopo Wangs,” talk returns once more to the South Side’s do-it-yourself approach to urban renewal.

“Honestly, it was all him,” Flamm says of Kimski owner Ed Marszewski, who was among the first to roll the dice in Bridgeport, converting his mom’s run-down bar into Maria’s in 2010, when the area was still on the wrong side of gritty. “Ed knew people wanted things to be different in the neighborhood and he believed in it,” Flamm says. “So guess what? He just went ahead and did it.”

A Legacy of Culture in Hyde Park
Jamila Woods, 29
Singer, Songwriter and Poet

Growing up in the south side district of Beverly, Jamila Woods always felt more at home in Hyde Park, a scenic neighborhood butting up against Lake Michigan to the east. A singer, songwriter and poet, Woods has been coming to the area since she was a teenager, drawn by cultural attractions like the Museum of Science and Industry and the Hyde Park Jazz Festival, but also a sense of belonging that was lacking in the historically Irish community in which she was raised.

“I always romanticized Hyde Park,” she says. “It felt like this second downtown to me. But one that was for black people.”

Woods now lives in fashionable Pilsen, but she still finds reasons to head south. One of these is Peach’s at Currency Exchange Cafe, a charming worn café just west of Washington Park, known for its soulful comfort food (shrimp-and-cheese grits, biscuits and gravy) and for being a part of the University of Chicago’s Arts Block initiative, which aims to establish a cultural corridor along a stretch of East Garfield Boulevard. “To me,” she says of how at home she feels in the area, “that is the most beautiful thing.”

Driving east through the 345-acre Washington Park, Woods points out the DuSable Museum of African American History, whose collection ranges from contemporary art to African tribal masks to civil rights-era photographs. The influence of her childhood visits to the museum is apparent in the songs on Woods’ new album, LEGACY! LEGACY!, each of which points to a prominent black historical figure. “It was a spiritual experience, channeling these people who inspired me,” she says. “I can hear the growth in my voice.”

Once home to the likes of author Carl Sandburg and civil rights lawyer Clarence Darrow, Hyde Park has long been a wellspring of progressive thought. In 1910, Frank Lloyd Wright built his famous Robie House here (daily tours are available). Three decades later saw the opening of the Hyde Park Art Center, an alternative arts venue that continues to showcase emerging talent.

Even the shops in Hyde Park have a cultural element to them—such as the Silver Room, a boutique selling everything from accessories to artworks, which also hosts exhibitions and performances. “I love shopping here because I know I’m getting unique pieces,” says Woods, who has appeared at the store’s annual Sound System block party and has worn its African-inspired jewelry in several of her music videos. “But I’m also giving money to a space that creates beautiful experiences for the community around it.”

Hyde Park today is very different from the place Woods fell in love with as a child. On East 53rd Street, we pass a parade of businesses like Chant, a restaurant serving global cuisine with an Asian twist, Hyde Park Records, a magnet for hipsters and Neil Diamond lovers, and Bibliophile, a bookshop-restaurant that serves gastropub food and cocktails named after famous books (such as the bourbon-based Great Expectations). “It’s definitely a different vibe now,” Woods says. “It’s like a whole new strip.”

We stroll for a while, taking in the grand University of Chicago campus, the side streets lined with Carpenter Gothic homes, then head east to Lake Michigan—or, specifically, Promontory Point, which provides stunning views of the Chicago skyline. “It’s one of the most beautiful places in the city,” Woods says, gazing out across the sky-blue water. “I just love it here.”

The Secret Cityscapes of Downtown
Michael Salisbury, 29

Michael Salisbury got the photography bug while attending college in Chicago’s downtown Loop area. The son of an architect, he was drawn to urban photography, so it didn’t hurt that he comes from a city with some of America’s most eye-catching architecture: the art deco Carbide & Carbon Building, the neo-Gothic Tribune Tower, the scallop-edged cylinders of Marina City. Yet he has never been interested in shooting these landmarks, at least not in any conventional sense. “I felt it was very much been-there, done-that,” he says.

At the intersection of Washington Street and Wabash Avenue, the “L” train rumbling overhead, Salisbury explains how he spends much of his time seeking out Chicago’s hidden cityscapes. “The Loop was where I created my photographic style,” he says, referring to images that present the city from strange vantage points, creating a clash of perspectives, or in which buildings are blurred or obscured, resulting in the kind of off-kilter beauty you wouldn’t normally find on postcards. 

At the Madison/Wabash CTA stop—part of the “Loop” system that gives this downtown neighborhood its name—Salisbury stands on a bridge overlooking the tracks.

“Capturing the trains going back and forth, the whole bustle of the city,” he says, “this really does it for me, honestly.”

Since Chicago was established in 1830, this area has been at the heart of its commercial life, driven in large part by generations of immigrants who settled here. After the devastating Great Chicago Fire of 1871, the city embarked on a building spree that would result in the world’s first modern skyscraper, along with cultural institutions like the Art Institute of Chicago and, later, the Majestic Theater, now the CIBC, which hosts daily performances of Hamilton.

We stroll among these buildings for a while, Salisbury pointing out angles and architectural details, then pop into the smart coffee shop Intelligentsia, where he always orders a dark-roast black (“I’m a simple man. What can I say?”). A block east of here is Millennium Park, known for its artfully landscaped green spaces, along with some of the city’s most innovative urban design features, including Frank Gehry’s brushed steel bandshell the Pritzker Pavilion, his snaking BP Pedestrian Bridge and the mercurial blob of Anish Kapoor’s sculpture Cloud Gate (a.k.a. The Bean).

While Salisbury is as appreciative of these masterpieces as the next Chicagoan, as a photographer he views them as a challenge. “Places like this force the photographer to be more creative,” he says. “There are so many ways to create something unique from a place that’s photographed thousands of times a day.”

While the Loop has a great food scene—which will expand this month with the opening of the gourmet food hall Politan Row—Salisbury tends to take a more literal approach to elevated cuisine. Our next stop is the 22-story LondonHouse Hotel, whose tri-level rooftop bar provides photogenic views of the buildings lining the Chicago River. “I’m usually in a hoodie and all black so I’m clearly not a guest,” he says with a laugh, digging into a short-rib burger. He is also a fan of Cindy’s, a swish American restaurant at the top of the Chicago Athletic Association hotel, which overlooks Lake Michigan.

Closer to the ground, Salisbury can often be seen aiming his camera at Chicago’s famous sculptures, including The Picasso, named for the artist who created it, and Alexander Calder’s 53-foot Flamingo. “I love how you can manipulate these structures to become something that looks uncanny or otherworldly,” he says. “Sure, maybe it’ll be a bust and I’ll walk away with nothing. But maybe I’ll walk away with something spectacular.”

Quirky Character in Bucktown-Wicker Park
Kelly Whitesell, 41
Boutique Owner

“Was this made for me or what?” It’s unclear whether Kelly Whitesell is referring to her Shady Lady cocktail or the place she’s drinking it—could be both. The Charleston Bar has been a staple of the Bucktown area since the late 19th century, but like the historic neighborhood around it, this snug local joint is still very much alive. “People used to think this was a no-man’s land,” says Whitesell, referring to Bucktown’s former reputation as a seedy area. “But hopefully we’re changing that.”

As founder of the lifestyle boutique Eskell, Whitesell has certainly played a part in the turnaround. “Yeah, I would say she’s got some neighborhood cred,” says our bartender, Mike. A Northwest Indiana native, Whitesell opened her first Chicago store 14 years ago, and last year moved from a modest space in neighboring Wicker Park to an airy converted muffler shop in Bucktown, which allowed her to expand both her inventory and her fan base.

The interior of Eskell is like an enlightened aunt’s brownstone: funky accessories, vintage furniture, potted plants. Whitesell, dressed in a dark silk button-up and black high-waisted jeans, bustles around the store, her wrists jangling as she moves. To satisfy her self-confessed bracelet habit, she heads to local boutiques Moth and Robin Richman, both of which have a gallery-like feel to them, a common theme around here.

Bucktown-Wicker Park has been a haven for creatives since the 1980s, when the Flat Iron Building started offering rock-bottom rents to artists and musicians. Though the area is dotted with cool art spaces like Bucktown Gallery and Jackson Junge Gallery, the Flat Iron is still the heart of the local scene, drawing people from all over town with performances and studio events. Inevitably, the area is also luring property speculators, but Whitesell doesn’t see this as much of a threat. “People are still very protective of this neighborhood,” she says.

To demonstrate the resilience of the creative spirit here, Whitesell takes me to Sideshow Gallery, a curiosity shop that specializes in spiritual objects. “I like to come and see what kind of weird stuff they have,” she says (a candle bearing the image of Stevie Nicks is one of the store’s items decorating her home). As Whitesell examines a sheep’s horn, store owner Anne-Katrin Elliot suggests she pop into her friend’s shop next door: Revolution Tattoo. Both women laugh at the idea.

Our next stop is Una Mae’s, a hip vintage store in Wicker Park. “I like to get lost and see what kind of treasures I come out with,” Whitesell says, rooting through the clutter. “People are always like, ‘Where did you find that?’” Then there’s Kokorokoko, whose interior looks like a Duran Duran album cover and whose inventory leans towards ’80s and ’90s kitsch. She’s come to this store a lot over the years, she says with a smile, “for inspiration.”  

As dinnertime nears, Whitesell reels off a few local options: fiery pork ramen at Furious Spoon, langoustine with orange blossom at the Michelin-starred Schwa, sausage-stuffed porchetta at foodie favorite The Bristol. Finally, we decide on moules à la provençale at the lively local bistro Le Bouchon. “I can’t eat mussels anywhere else,” Whitesell says, nursing a glass of pinot noir at the busy countertop. “I also love the steak,” she says with a sly smile, “even though I don’t eat red meat.”

From here, my thoughts turn to another local selling point: the bars. I am particularly keen to try The Violet Hour, both for its award-winning cocktails and its amusingly stringent house rules. In an age when Instagramming your drink is a prerequisite for a good night out, the bar’s no-cellphone statute might look like a bad decision, but for Whitesell it’s an expression of what makes her neighborhood pop.

“I love it here because every single house, every person, every business is different,” she says. “It screams authenticity.”

Shopping with a Difference in Humboldt Park
Catie Olson, 45
Bartender, Artist and DJ

After she graduated from college in the mid 1990s, Catie Olson—who hails from Central Illinois—knew she wanted to cast a wider net. A multimedia artist and DJ who strikes up conversation with pretty much everyone she meets, Olson chose Chicago as her new home. “I felt it was where I belonged,” she says.

Two decades later, sitting at the malt shop-style counter of the diner Spinning J, Olson describes how neighborhoods like Humboldt Park, with its locally run businesses and tight-knit communities, have made this vast, fast-moving city feel more like a village. “Chicago, oddly, never feels very big to me,” she says, dipping into a bowl of broccoli-cheddar soup. “And as you get to know more and more local businesses, your arms keep stretching out farther to embrace them.”

Located on Chicago’s northwest side, Humboldt Park has been home to generations of immigrants, starting with Germans, Scandinavians and Italians, and later Polish and Russian Jews.

By the 1950s, Humboldt had a sizeable Puerto Rican population, and that community still has a vital presence: The Puerto Rican People’s Parade takes place here each summer, along with the huge Fiesta Boricua block party. In the 207-acre park that gives the neighborhood its name—amid lagoons, woods and rolling grassland—stands the National Museum of Puerto Rican Arts & Culture.

Olson, who works as bar manager at the nearby wine bar Red & White, has a list of things she loves about Humboldt, such as the abundance of offbeat shops like Richard’s Fabulous Finds, a vintage menswear store whose dapper proprietor, Richard Biasi, is a well-known local character. She also likes The WasteShed art supply store, whose stock consists of items salvaged from local schools, and Adams & Son Gardens, a colorful garden center that’s been here for over 25 years.

“In the summer, they have all their outdoor plants and herbs and tomatoes outside and it’s just beautiful,” Olson says, browsing the center’s succulents while making small talk with the owner. The nearby wine and beer bar Rootstock makes a point of stocking its garden with plants from here, she says, an example of the collaborative spirit among local businesses. “You watch out for each other and everyone thrives. It’s a win-win.”

From here, we head a few blocks south to Space Oddities, a bookstore-curio-shop-gallery owned by her pal Sarah Luczko, which sells everything from novelty underpants to vintage videocassettes. “No joke, I once bought a Peruvian cow horn from here that I’ve used in one of my experimental music ensembles,” Olson says, taking a whiff from a stick of sage.

Finally, we stop by the record and clothing store Wild Prairie Vinyl & Vintage. Olson is friends with store employee and local DJ Kevin Jacobi, whom she met at one of her regular DJing gigs. She can’t recall the exact venue—it could have been the Sportsman’s Club, known for the deer heads on the walls and the craft cocktails behind the bar, or maybe the storied music venue Empty Bottle.

“Make yourself at home!” Jacobi cries as we enter, psychedelic music blaring from the sound system. “Honestly, I’m just happy this sort of place still exists,” Olson half-shouts as we browse racks of T-shirts and boxes of records. “The vibe lives on.”

Heads up

A private guide to Chicago’s microbrew scene

When it comes to Midwestern beer towns, the glory usually goes to Milwaukee rather than Chicago. Johanna Wawro—a bartender and guide for Tours by Locals—says the city is actually a Shangri-la for craft beer lovers, a point she makes repeatedly on the company’s four-hour tours of local breweries.

Wawro starts today’s tour with a quick history lesson: Thanks to lager-loving German immigrants who arrived in the 1830s, Chicago had 60 breweries by 1900. “But then prohibition happened and everything went belly-up.” It wasn’t until 1988 that Goose Island Beer Company took a gamble and paved the way for today’s thriving scene.

My first tipple is at Kickstarter success Pipeworks Brewing Co., in the Hermosa neighborhood. The brick warehouse exterior belies the brewery’s funky spirit, reflected in brews like Spumoni Jones Dog (chocolate milk stout with pistachio and cherry added). I opt for a honey-infused double IPA, which has herbal undertones.

Next comes the Lincoln Square brewery Half Acre, where I throw back a glass of Volo, a wheat beer with citrus notes. Farther south we find Marz Community Brewing (pictured), whose industrial-chic taproom offers scores of delicious beers—I try the Jungle Boogie, a pale wheat ale flavored with rooibos tea. Our tour ends at Revolution Brewing in Avondale, where I down a perfectly smooth glass of Eugene, a chocolate malt porter. “If you build it,” Wawro says, gesturing at the crowd around us, “they will come.”

Photography Lucy Hewett

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