Ash Hiden explores why America’s Second City should be first on your list for a stateside city break following the massive success of culinary drama The Bear
The Bear is an astonishingly good watch. As hard to turn away from as lead star Jeremy Allen White’s Calvin Klein underwear ads, it is a celebration of Chicago’s brilliant but under-appreciated foodie scene. With a third season of the multiple Emmy and Golden Globe winning show back on screens, I took the opportunity to check out Chicago: the city of the Bears, the Bulls, but particularly the Italian beef.
Let’s talk about the meat. On The Bear, Jeremy Allen White’s Carmy character forsakes his career as a fine dining chef to run the humble sandwich shop left to him by his late brother. The Italian beef sandwich epitomises Chicago; locals prefer to be known for this than deep dish pizza. “I’ll take out-of-state relatives for deep dish but that’s about it,” one resident told me.
Not long after touching down, I was dining at one of the best sarnie joints in town. Portillo’s is a ‘local boy makes good’ story spanning 50 years. There are branches in Chicago and the Midwest, some southern states and the East Coast. Four-hour slow-roasted beef is thinly cut, generously piled into a fresh baguette, and best served “hot and wet” with spicy peppers and dipped in gravy.
Foodie Chicago, from Mexican influences to fois gras bao buns
Carmy turns his sandwich shop into a proper gastronomic restaurant in The Bear, and many of the city’s best restaurants have doubled as actual filming locations for the series. So why’s the food so good? Cheaper rents relative to NYC allow restaurants to experiment more creatively. Chef Andrew Zimmerman of the Proxi restaurant on W Randolph Street in West Loop Gate serves excellent small plates inspired by the chef’s travels. The foie gras bao buns with Szechuan cucumber and apple hoisin were out of this world and sat particularly well with scallops in a creamy laksa broth and tempura elotes.
Chicago has a strong Mexican community, and in the neighbourhood of Pilsen in the Lower West Side, I took the Tacos & Tequila walking food tour with a potent margarita from 5 Rabanitos in hand. I made tamales at Chef Alonso’s sister outpost of Fiesta Tamaleria El Barrio before visiting the highest density of murals in the city, including a mile-long stretch on W 16th Street. Five minutes’ walk from here is Taqueria Los Comales, specialising in delicious ground beef tacos with homemade salsa verde and rojo. I could have spent all day in this unpretentious, buzzy locals favourite, people watching and feeling compelled to copy-order what everyone around me was having.
Once the bar staff got over my West Country accent, we ordered drinks, and I asked what encapsulates the soul of the city
I retreated to The Peninsula for R&R. On E Superior Street on Chicago’s Magnificent Mile of N Michigan Avenue, the hotel has a decent rooftop lounge with views of the structure formally known as the John Hancock Centre, a looming 100-story 1960s skyscraper that was formerly the second tallest building in the world following the Empire State Building. The observation deck on the 94th floor offers views across Lake Michigan, a short walk from The Peninsula, great for strolls and beach time.
Chicago beyond The Bear
Despite being a third the size of London, Chicago feels expansive, but that’s not to say you can’t get into nature. Vertically, the city outdoes London by literal miles. Take in the truly unusual architecture on the Chicago Architecture Foundation Centre River Cruise, including the wavy facade of the tri-towered St. Regis Chicago, a building unlike anything I’ve seen anywhere else. At 1,191ft tall, it is the tallest skyscraper in the world designed by a woman, the architecture academic Jeanne Gang. Around the corner from where the river cruise starts and ends, a collection of large-scale portraits stretches along the riverwalk between E Lake Street and N Franklin Street. They constitute a gallery of lesser-known but notable Chicagoans who embody the city’s spirit, spanning the past and present — from artists and activists to workers and first responders.
Entitled ‘The People in Your Neighborhood’, the installation was unveiled in the otherwise dark summer of 2020 and is the work of local artist Dont Fret. I reached out to him and we met in Richard’s Bar on N Milwaukee Ave. The venue itself was a personal highlight of my time in Chicago: it was a 93-year-old American bar with the classic tin ceiling and the Rat Pack swinging out of the jukebox.
Once the bar staff got over my West Country accent, we ordered drinks, and I asked Dont Fret about the installation’s impact and what encapsulates the soul of the city. “I’m really proud of the project”, he says over a beer, then later a bourbon. “We are the sons and daughters of hustlers and schemers, the people who get perilously close to getting it all right; but rarely do. That’s our burden! At least our buildings are so tall we can go to the top, maybe see eye-to-eye with god. This is the best city on the planet, and we aim to keep it that way. Perfectly imperfect.”
Just like those messy beef subs then: tricky to hold and likely to fall all over your shirt, but utterly delicious too.
Rooms at The Peninsula start from £351, visit Choose Chicago for further information on what to do; choosechicago.co
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