Chicago is the best city in the USA.
Reader, before I get into why, I have a confession to make. I have never stepped foot in New York. In fact, I’ve not spent much time in the States at all, except for a few days in LA, Nashville, San Diego, and Scottsdale. But I stand by it. Mainly because I refuse to believe a better city exists on this side of the Atlantic.
Some could say my love for Chicago is impulsive and irrational, like a boozy, late-night trip to the casino. And in a way, they’d be right. It is a devotion built not necessarily on objective facts but on a feeling – something that’s hard to put into words. It is innate and embedded in my soul. We are just, for whatever reason, kindred spirits.
Still, there are some specific reasons why I, and many others, feel so enamoured by the City of Big Shoulders. To start with, Chicagoans are different from typical city folk. They will moan about politics, but they will also smile at you on the L (an elevated rapid transit system). They will ask you how you’re doing and care about your response. They will allow you into conversations you have no right to be in and cut you off if you’re talking shit. They will compliment you on your sunglasses and take the piss out of your shirt. They will invite you to a game of pool if they see you looking lost. But they’ll leave you alone to ponder your thoughts if you seem content. Head to some of the neighbourhood dive bars and you will, I guarantee, leave with new friends. It was in these very dive bars, places like the Rainbo Club on Damen Avenue, that I first fell in love with Chicago.
Chicago does dive bars like no other place I’ve been. They can be raucous, often boozy, always fun. Drinking a shot of pungent, aniseed-tasting liqueur that goes by the name of malört feels somewhat of a rite of passage to first-time visitors to the city. You must try it, perhaps as part of a Chicago handshake – a combo of malört and a beer like Old Style or Miller High Life – at least once. Except at Rossi’s, a small, unassuming downtown bar with walls cluttered with beer memorabilia and ceilings draped in flags. Here, you should head to the fridge and pull out a Milk Stout Niro, a smooth, sweet stout. Late nights here are best spent mingling with locals – medical staff from the nearby hospital, city slickers, bartenders and musicians – until the dawn breaks.
There is, however, one drinking spot I love more: The Old Town Ale House. This place feels like a Chicago institution. It’s in a quieter part of town opposite The Second City, the infamous comedy club, where Bill Murray, Tina Fey, and John Belushi cut their teeth. The late chef and documentary maker Anthony Bourdain loved Old Town, and it’s easy to see why. This dark, woody bar pulls an excellent Guinness, has a warm vibe and attracts a diverse crowd.
There’s usually at least one fanatical Bourdain fan sitting at the bar alone and engaging the bartenders in lively conversation. You’ll also spot first dates snuggling in dark corners under gentle red lights and clusters of rowdy Chicagoans making wisecracks and shooting the breeze into the small hours.
On visiting, order a pint, then head immediately to the jukebox to bang on some records. Tom Waits, The Band, David Bowie, it’s your choice, three tracks for a dollar, then sit at the bar and allow your eyes to run along the walls clad in caricatures of big-hitting comedy legends. They sit alongside paintings of long-gone regulars and satirical political portraits. My favourite is Putin in a tutu, which sounds like a song by The Smiths.
While Chicago’s nightlife and its many brilliant live music venues – the Empty Bottle, Green Mill, Kingston Mines, or Buddy Guy’s Legends – are what first captivated me, the city’s raft of wholesome activities consolidated things. On sunny days, the beach beckons (Chicago has over 20 beaches on the banks of Lake Michigan). Active folk may even jog or cycle along the 18-mile lakefront trail. However, I’ll more likely find a peaceful spot in one of the neighbourhood parks to sit and read or people-watch.
Millennium Park, which turned 20 this year, is one of my favourites as it’s skirted by skyscrapers yet somehow feels remote. It’s also home to the city’s iconic ‘Bean’ sculpture and Frank Gehry’s futuristic music venue, the Jay Pritzker Pavilion, which looks like something from the Transformers. The latter has free live music concerts in the summer, from laidback jazz to heel-stomping rock ‘n’ roll shows. A few years ago, I stumbled across one of my favourite bands, Chicago-based Whitney, playing here for free. This serendipitous encounter seduced me even further.
Just a short stroll from the Jay Pritzker Pavilion is arguably one of the world’s most impressive art galleries. The Art Institute of Chicago is the perfect rainy-day activity. You must, however, set half a day aside to get around as there’s a lot to see. It houses some of the greatest paintings of modern times, from Monet’s Water Lilies and Nighthawks by Edward Hopper to Grant Wood’s American Gothic and Georgia O’Keeffe’s Sky Above Clouds IV. If short on time but thirsty for culture, the WNDR, a smaller multi-sensory, immersive gallery with works by Yayoi Kusama, is superb.
Chicago’s iconic skyline is another thing that always blows me away, so I’d implore any new visitor to the city to take the architectural boat tour. You don’t just learn about how Chicago’s river flows backwards and is dyed green every St. Patrick’s Day, but how a devastating fire in 1871 is partly responsible for the diverse infrastructure that stands today. From the neck-craning Willis Tower to the 100-story John Hancock Center and the brutalist dream that is Marina City (or the Jetson Towers). Fans of the written word will also enjoy wandering around the American Writers Museum or jumping on the L train up to Oak Park in the suburbs to see where Ernest Hemingway was born.
Food will likely be on your mind after all of that. Thankfully, Chicago is regularly voted amongst the USA’s best foodie cities. If you’re a meat eater, it is essential to visit Mr Beef to try a moist, doughy Italian beef sandwich slathered with sweet peppers — made famous by the shouty, sweary folk in The Bear. For something more flashy, there is also an abundance of fine-dining restaurants. Damarr Brown’s unpretentious, award-winning Virtue, specialising in hearty Southern cooking, is among the best.
Elsewhere, Daisies, a solid mid-range option, serves quality pasta dishes and an unusual cocktail: a mushroom margarita. I can’t recommend the tacos from Antique Taco in Wicker Park enough, either, especially if you’re feeling a little dusty from the night before. Deep-dish pizza isn’t for me but Pequod’s, or Lou Malnati’s are the go-to spots. For classic Chicago hotdogs, everybody knows to head to Portillo’s.
To feel like a real Chicagoan, you could – and you should, always – head to Wrigleyville to watch the Cubs. Few experiences are more wholesome yet pulsating than hearing “Take Me Out to the Ball Game” at a packed Wrigley Field for the first time. After the game, I usually head to Sluggers, a bonkers sports bar with arcade games and a batting cage upstairs. I’ll usually grab a Pabst Blue Ribbon, exchange a few bucks for some plastic counters, and step up to the plate to hit (or try to hit) a few baseballs.
It was here, towards the end of my first visit to Chicago, when my deep affection for the city was sealed. When, after a few beers at a Cubs game, I nervously pulled on a helmet and headed to the bar’s batting area for the first time. A cackle of rowdy ball fans rattled the cage and heckled me from the sidelines. Until I caught a beauty right out the middle of the bat and they erupted like I was Ron Santo hitting a home run at Wrigley Field.
These magical moments, of which I have many, are what I love most about Chicago and why – at least in my eyes – it is the best city in the USA. Don’t believe me? Go and see it for yourself.
For more information on Chicago, please visit www.choosechicago.com
