There’s something about Chicago, the main hub and corporate headquarters of United Airlines, that makes it feel emblematic of the United States as a whole. Maybe it’s because the city’s 19th-century rise was defined by its prominence in building the nation’s railroads, packing its meat, and making its steel. Or maybe it’s because steady waves of immigrants have been shaping the area ever since a Haitian trapper established a trading post on the Chicago River in 1779. These days, this lakefront metropolis of 2.6 million has spread across 100 neighborhoods that are as distinct from one another as they are united by an ever-present drive to create. The type of production has changed through the years, but Chicago remains a city of makers, a hub of culinary and comedic talent constantly finding new ways to honor and interrogate its past.
Day 1
Fine art, an architecture cruise, and Al Capone’s favorite jazz club
Lake gulls swoop overhead and cyclists hum past me as I jog along glittering Lake Michigan. Chicago’s Lakefront Trail is one of the city’s signature green spaces, running nearly 20 miles along the western shore, with skyline views and sandy beaches dotted throughout. Just as I’m passing Ohio Street Beach, where two dogs are frolicking in the water, a girl jogging past me exclaims to her friend, “Dude, this is beautiful!” I couldn’t agree more.
It’s a quick run back to my hotel, the Pendry Chicago, inside Michigan Avenue’s Art Deco Carbide and Carbon Building. I grab a cappuccino and a croissant from its airy French café, Venteux, and freshen up before heading over to Millennium Park, where I pass families taking photos of their reflections in Anish Kapoor’s Cloud Gate—aka The Bean—and admire the undulating steel Pritzker Pavilion, which hosts a slate of free concerts every summer.
Walking south on Columbus Drive, I reach the Art Institute of Chicago, which I enter via the Renzo Piano–designed Modern Wing. With nearly 300,000 pieces in its permanent collection, the Art Institute could fill days of exploration. I merely attempt to squeeze in a few of its greatest hits: Marc Chagall’s America Windows, which look more like watercolor than stained glass; the gauzy pointillism of Georges Seurat’s A Sunday on La Grande Jatte. Of course, I also hit the fabulously detailed Thorne Miniature Rooms, 68 tiny interiors—ranging from a 13th-century English Catholic church to a 1940s Modernist California living room—created by Chicago socialite and artist Narcissa Niblack Thorne. I can’t look away from the postage stamp–size paintings and tiny cutlery; it feels as if a thumb-size person could enter and start going about their business at any moment.
Next, I’m off to visit another local icon: Al’s #1 Italian Beef. Thanks to the Chicago-set hit TV series The Bear, the Italian Beef sandwich is having a moment. Al’s has been serving the Second City staple—thinly sliced roast beef on a French bread bun, dipped in jus and topped with spicy giardiniera and sweet peppers—since 1938, initially as a front for a bookmaking operation. I hop on the Red Line for a two-stop ride to the River North shop, and order “a regular beef, regular wet” (translation: a 6-inch-long sandwich, dipped in jus). The pillow-soft bun is the perfect complement to the spicy peppers and rich, juicy beef. Much as with an ice cream cone, eating a wet Italian beef is a race against the clock, and I inhale mine standing up at the counter.
From Al’s, it’s a 20-minute walk to the launch site for the Chicago Architecture Center River Cruise, beneath the DuSable Bridge. Seated on the roof deck, a local Revolution Brewing pilsner in hand, I spend the next 90 minutes learning how to read the skyline from Kent, our fast-talking volunteer docent. “Modernists,” he tells us as we cruise past the residential Lake Point Tower skyscraper, “are always trying to show you how the building stands up.” Postmodern buildings, on the other hand, try to fit in with their surroundings—the green, reflective glass on the Gateway Center IV building being a prime example. Interspersed with Kent’s architectural criticism is a historical overview that includes the devastation of the Great Chicago Fire of 1871 and the decision to reverse the flow of the Chicago River, away from the lake, in order to maintain the city’s drinking water. Of the river’s cleanliness today, he advises: “Just don’t drink it when you’re in it.”
After the tour, I’m inspired to visit one of the buildings we saw: The St. Regis Chicago, a turquoise-tinged, wavy skyscraper that’s the world’s tallest building designed by a woman, architect Jeanne Gang. A short walk down the pedestrian-only Riverwalk toward the lake brings me to the hotel, whose Japanese-inspired Miru restaurant has the perfect terrace for taking in the coming golden hour. While admiring the views of Navy Pier and the lake, I sip a Smoke on the River cocktail made with tequila, mezcal, persimmon liquor, lime, agave, and togarashi seasoning.
I could linger on the terrace all night, but it’s time to head back across the river, where I’m meeting a few college friends who are in town—JT, Amelia, and Kimberly—for dinner at Indienne. Amid blush-colored banquettes and abstract Holi-inspired artwork, chef Sujan Sarkar has brought his blend of Indian flavors and European techniques to Chicago’s teeming tasting-menu scene, earning a Michelin star within just a year of opening. Our six-course adventure kicks off with the arrival of the Gin Trolley, summoned by Amelia, who creates a custom concoction featuring saffron-infused Tanqueray and kokum fruit. (Kimberly and I opt for the wine pairing, which ranges from a sweet, sparkling Shirakabegura sake to a juicy Sicilian nerello mascalese.) The first bite, a pani puri–inspired buckwheat tart with a blackberry “bubble” that explodes in your mouth, prompts JT to exclaim, “How do they do that?” Our server reveals no secrets. The meal progresses with scallop marinated in balchao (a Goan sour chili sauce), shami lamb kebab with a mint sauce I want to lick off the plate, and chicken makhani layered with pistachio and the creamiest dal I’ve ever tasted. By the last bite, I’m ready to pass out on the banquette.
There is, however, one more very important stop left to make. We take a 20-minute Uber ride to Uptown, where the flashing lights of the Green Mill Cocktail Lounge beckon. First opened in 1907, the bar became infamous during Prohibition, when one of Al Capone’s associates turned it into a speakeasy. We settle into bar seats across from what was allegedly Capone’s favorite booth and nurse Stellas as guitarist Joel Paterson and his band launch into some Chet Atkins, followed by the Western Swing classic “Saturday Night Rag.” “We’re pushing country music on you tonight—I’m not sure why,” Paterson tells the crowd. Based on the volume of the applause, I can safely say no one minds.
Day 2
Mexican muralism, carnitas, and comedy
I greet the day from a several blocks–long line at Kasama, the world’s first Michelin-starred Filipino been shaped by Mexican restaurant. Husband-and-wife chef duo Genie Kwon and Tim Flores offer a tasting menu each night, but during the day Kasama is Mexican art collection in a bakery and walk-in café—although, after the place was featured in Season 2 of The Bear, “walk-in” means “wait for an hour outside.” “We were busy before, but The Bear brought a whole other demographic,” Kwon says. “You can tell who is visiting because they’ve seen the show based on their orders. The effect that came from it is more than we could have ever expected.” By the time I reach the front of the line, I’ve worked up a serious appetite, and I overcompensate, ordering a longanisa sausage breakfast sandwich, a matcha-pandan eclair, and an ube-huckleberry Basque cake. I stow that last one in my bag for later, and hop in a rideshare headed 20 minutes due south, to Pilsen.
A neighborhood that’s been shaped by Mexican immigrants since the 1960s, Pilsen is home to the National Museum of Mexican Art, which boasts the largest Mexican art collection in the U.S., with more than 18,000 pieces. The current exhibition from the permanent collection explores the evolution of Mexican identity in North America through pieces such as Day of the Dead trees of life and Jesús Helguera’s La Leyenda de los Volcanes, a painting that depicts characters from a popular tragic myth. I’m most drawn to the work of local Xícágo artists devoted to capturing life in the city: There are images of the South Side from photojournalist Antonio Pérez and a multimedia piece by Marcos Raya that incorporates dirty gloves and machinery parts, a reference to the industrial work many Mexican immigrants have had to take on in order to achieve the American Dream. Another gallery tells the story of Mariachi Potosino, a musical group founded by Durango native José Cruz Alba that became a Chicago institution.
On my way out, I meet Mario Hernández, a Pilsen native and a gallery education coordinator at the museum who has offered to show me some of the murals that have become a signature feature of the neighborhood. He explains that Pilsen’s first mural was painted in 1968, when increasing numbers of Mexican immigrants were arriving in Chicago, including artists who continued their home country’s long tradition of muralism here.
“The content of the murals changes depending on the area and its people changing,” Hernández says, noting that, for more than a decade, gentrification has been a hot topic in the neighborhood.
The uneasy mood around neighborhood change is captured in a mural right across the street from the museum. The painting, by artists Hector Duarte and Gabriel Villa, spans two stories of the Pilsen Housing Cooperative. Its right side depicts a building emblazoned with a sign bearing the mural’s name, Fight to Stay, which Hernández says refers to “the real estate developers trying to buy people out.” Behind those words, tornadoes approach, which Hernández explains represent the displacement of families in Pilsen. Below, monarch butterflies serve as a nod to migration, and on the corner of the building the branches of a large tree stretch across the walls, representing the tree of life and connection to one’s roots.
We continue along 18th Street, passing depictions of folkloric dancers and mosaics of Pilsen residents, before Hernández leaves me at Carnitas Uruapan, which has been slinging Michoacán-style roast pork since 1975. As soon as I walk in, I’m greeted with a sample and an explanation of the five different cuts from the pig. I settle on the Especial platter: a half-pound of carnitas, a fried potato taco, refried beans, chicharrones, piping-hot corn tortillas, and a hibiscus agua fresca.
I spread this feast out on a bench in Harrison Park, a few blocks to the west, and begin assembling my tacos, topping each one with fresh onions, tomatillo salsa, pico de gallo, and lime.
From here, I hop in an Uber, headed to the North Side’s Logan Square, known for its trendy bars, quirky boutiques, and, yes, acclaimed restaurants. Upon arriving at Logan Square Park, which is dotted with picnic blankets, I see a tattooed dog owner walking a poodle whose head and tail are dyed pink. I pop into Wolfbait & B-girls, just off the park, and browse locally designed gifts— earrings made from old Barbie shoes and vintage Chicago Parks posters—while trying to eavesdrop on the tarot reading happening at the counter. Then I poke my head into City Lit Books, where I pick up a copy of The Mountain Goats frontman John Darnielle’s novel Devil House from the staff picks shelf. I overhear a woman with a cat on a leash tell one of the shop clerks, “He’s good on the L.”
I walk on down North Milwaukee Avenue—known as the “Hipster Highway”—to Daisies, which bills itself as a “Midwestern Italian” restaurant and is beloved for its housemade pastas. Golden light streams through the large front windows, casting a magical glow on the exposed brick walls and the diners deep in conversation. I take a seat at the roomy bar and start with a Physician’s Friend cocktail, which blends gin, alpine liqueur, and parsley soda. Next arrive pillowy gnoccho frito (served with carrot confit) and rigatoni covered in a fermented tomato sauce with spicy ’nduja and bright, crispy lemon breadcrumbs. To round out the meal, I savor a square of Gooey Butter Cake from the “Treats” section of the dessert menu.
In the deepening dusk, I stroll another few blocks farther down North Milwaukee Avenue to The Lincoln Lodge, an indie, comedian-run comedy club. The club has existed for 23 years, churning out stand-up stars such as Hannibal Buress, Chelsea Peretti, and Kumail Nanjiani, although it only found a permanent home at the border of Logan Square, Wicker Park, and Bucktown in 2020. I watch comedians greet one another in the wood-paneled bar at the front of the room before they file into the small theater for “Sloppy Sundays,” billed as a weekly show of “alternative stand-up comedy.” Seven stand-ups rip through rapid-fire sets on topics including hair loss, public bathrooms, and Catholicism. While essentially none of what they say is printable here, I swear that by the end of the show I’m crying tears of laughter into my Miller High Life.
Day 3
A new national park, Frank Lloyd Wright, and Southern cooking
First thing, I move my bags to The Publishing House Bed & Breakfast, located in the West Loop, a former meatpacking district that’s now a culinary hot spot. A 15-first planned industrial minute walk northeast from there is one of the spots that paved the way for the neighborhood’s reimagining as a dining destination: The Publican, a beer-driven restaurant inspired by European taverns. I take a seat on the front patio and start with a Brunchbox cocktail (pilsner, amaro, grapefruit) before ordering a little gem and fennel salad topped with crunchy pig ears, a melt-in-your-mouth strawberry rhubarb bostock (a sort of fancy cousin to French toast), and a shakshuka with whipped feta and pine nuts. On a warm, sunny day, Fulton Market offers prime people-watching, but I can’t linger too long, as I’m off to explore another formerly industrial neighborhood—and Chicago’s only National Park Service site.
A 20-minute drive away, on the Far South Side, the recently designated Pullman National Historical Park tells the story of the first planned industrial community in the U.S. via public tours of the grounds and preserved homes. In 1893, the Pullman Company housed more than 12,000 railroad car manufacturers here. Although the company built its last car in 1981, about 900 people still live in the neighborhood, drawn in by its affordability and suburban feel. Tom McMahon, who greets me at the Historic Pullman Foundation’s exhibit hall, is one of those residents; his family is in its fourth generation at Pullman.
Before we head out on a tour, McMahon explains why company founder George Pullman wanted to build and operate a town that was “free from the ills of modern society” for his workers. By offering prime 19th-century amenities—indoor plumbing, steam heating, one of the country’s first shopping malls—he hoped to prompt better worker performance. “It’s no different than Google,” McMahon explains. “They want to create an environment where their employees want for nothing.” This experiment famously backfired in 1894, when, following an economic depression, Pullman cut wages while also refusing to lower rents, resulting in a strike that led the federal government to establish Labor Day.
As we walk the 12-acre site, past tidy red-brick row houses with green lawns, McMahon explains how the company’s hierarchy was reflected in the housing. Transient workers rented tenements, while on Supervisors Row the homes are three stories and have spacious front porches. We eventually make our way to the imposing Administration Clock Tower Building, now home to the National Park Service Visitor Center. We’re greeted by park ranger Elijah Olomoniyi, who leads us through the interactive exhibits, including a recreated Pullman luxury sleeper car and a dive into the history of the Pullman Porters—the Black male workers whose organizing laid the foundation for the Civil Rights Movement. “A lot of people discount Chicago’s South Side,” Olomoniyi says, “but it’s extremely historically rich. The difference between Pullman and a lot of other places on the South Side is that [other neighborhoods] didn’t have people to advocate for them.”
These words stick with me as I make my way to Hyde Park and another South Side historic landmark: the Frederick C. Robie House, the only Frank Lloyd Wright– designed house within the city limits that’s open to the public. The 1910 building, with its cantilevered roofs, is considered a quintessential example of Prairie-style architecture, which emphasizes horizontal plains, open floor plans, and natural light. During a 45-minute tour, I learn about how Wright took inspiration from Japanese design, and how he created a compression effect by using low ceilings to “build anticipation” as visitors enter. When our guide explains that the house has no basement or attic because Wright believed they would “create clutter,” it occurs to me that the architect may have been the Marie Kondo of the 20th century.
From the Robie House, I stroll east to the 550-acre Jackson Park, envisioned by Central Park designers Frederick Law Olmsted and Calvert Vaux. I wander the tranquil paths in the Garden of the Phoenix—originally part of the Japanese pavilion at the 1893 World’s Columbian Exposition—and pass the shining silver petals of Yoko Ono’s Sky Landing sculpture. Even the “keep off” signs inspire a sense of peace; one reads, “Shh, baby moss at rest.”
I pick up a Divvy bikeshare and ride north to East 53rd Street, which is lined with shops and restaurants, including former president Barack Obama’s favorite diner, Valois. At Hyde Park Records, a neighborhood staple for four decades, I pick up records from two iconic Chicago acts: The Staple Singers and Chaka Khan. Then I swing into the The Silver Room, a palo santo–scented boutique and community arts space, to browse jewelry and South Side–branded sweatshirts. I’m perusing silver cuffs when I realize it’s time for dinner, down the block at Virtue.
Chicago native Erick Williams’s restaurant has won James Beard Awards two years in a row for its nuanced and delicious exploration of Black American foodways. As I sip a Hyde Park Sazerac, the kitchen churns out a parade of refined Southern classics: blackened catfish with barbecued carrots, rich gumbo with chicken and andouille sausage, and fluffy pimento cheese biscuits. Cauliflower, brined and smothered in black garlic and served over a bed of jollof-style bulgur, is a surprise favorite. The mood in the dining room, decorated with sculptures by renowned Chicago artist Theaster Gates, feels so convivial that when a man at the table next to mine asks to try my collard greens, I don’t realize he’s joking.
I grab an Uber back toward the West Loop to end my night, fittingly, at After, the companion cocktail bar to the Michelin-starred tasting-menu restaurant Ever (which, despite what The Bear will tell you, is still open). The cavernous space feels like a sci-fi movie set, with low, blue-gray lighting and slender mirrors glittering behind the bar. I order the Hades—G4 blanco tequila, amaro, jalapeño, and shiso—which requires the vest-wearing bartender to affix a skull-shaped hibiscus ice cube to the glass with liquid nitrogen. I look around the room at friends and couples huddling in close conversation over their drinks, feeding on the energy of the room and a night that’s just beginning in this ever-evolving city.
