City & Politics, Essay

Testing, prodding the Winnipeg of the South

Chicago. Chi-town. The Big Chizzy. The great American midwest metropolis. The city known around the world as “The Winnipeg of the south.” But how did it come by this distinction? Is it worthy? How does it stack up against the original Winnie City? I went down there last week with my old friend, the hairstylist Caroline Thiessen, so I’ll tell you all about it.

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We drove down in the hairstylist’s car, a demon-red 1990 Toyota Tercel named “Little Wayne.” This was good, because like all big American cities, the best way to come into Chicago is by freeway. Freeways are such a beautiful literal and literary expression of the American obsession with freedom. And you can drive super-fast on them. We centerlane sauntered our way in, though, taking time to soak up Chicago’s impersonation of our skyline.

They got it all wrong. Chicago’s core is crawling with skyscrapers. It’s way too impressive. It sits out on the flats where the American prairie meets the Great Lakes like a bright-eyed hick comic-book illustrator’s conception of contemporary civilization. It looks like it’s probably patrolled by at least a couple caped heroes with the power of flight, or like something somebody built in Simcity 2000.

The hairstylist and I are both disastrously cool, so we couldn’t just stay anywhere in Chicago.  We had to stay in the hippest neighbourhood in Chicago. What is the hippest neighbourhood in Chicago? Many of you will probably guess Wicker Park, because that’s what most people believe, but most people aren’t hip. No, Wicker Park is now thought over-ripe by the highest ranks of the hipluminati, and the torch has been passed to a place called Pilsen. We stayed in Pilsen.

Pilsen is a working-class neighbourhood that warehouses a bunch of artists’ studio space and Chicago’s Mexican population. A big billboard under the freeway advertises “Teléfonos Android.” Everything on 18th street, Pilsen’s main drag, is either a gallery, a vintage store, a hair salon or a taqueria. Mostly it’s taquerias. The serving sizes of this Mexican food are large. A lot of emergent art could emerge of the average $6 snack here. But we couldn’t just stay in our enclave for the whole week, so the hairstylist and I hopped Chicago’s famous ‘L’ train and squealed off towards the teeming core.

Pilsen Store frontst
A Pilsen-neighbourhood storefront.

Downtown Chicago is referred to by locals as ‘the Loop’ after the loop that’s made by their transit system there. This part of Chicago is coming fresh off it’s starring role as Gotham City in Christopher Nolan’s Batman trilogy, and you see why Nolan would choose these deep steel valleys for his Dark Knight to tumble into on his batcycle. You also grasp immediately why he’d choose the huge glittering monoliths of Chicago as the perches on which his bat-suited billionaire vigilante could ponder and puzzle: just how many civil liberties does this unwashed mass beneath me deserve, anyway? How far should I go to protect them from themselves?

I ducked into a restaurant and ordered a Capone Burger with an Eliot Ness Lager as a way of signaling my neutrality. But I suppose I must address the people. The people! It’s in this sense that Chicago is most similar to Winnipeg. To look into the faces of Chicagoans is to see your fellow Winnipeggers.

In part, this is surely because Chicago was populated by similar immigrant communities. Chicago, too, is a blend of Poles and Ukrainians, Germans, and Jews. But this isn’t the key factor in their similarity, for people only shape a place for a short time, and then the place shapes them, and goes on shaping them so long as they dwell there.

Chicagoans, like Winnipeggers are people of the urban Midwest – people of the urban prairie. These people are clear-headed and practical. They’re a bit reserved at first, but they warm up after you’ve known them for about 15 years. They see the world as a cold material place, and act accordingly. My Winnipeggonian travelling companion, as if in some ritualistic dance of bleak material reality with Chicago, spent most of the trip checking her hair in the mirror, complaining that society only values women for their looks, and raving about her fears of losing her looks with age.

Chicago’s greatest writer, Saul Bellow said of it: “Chicago with its gigantesque outer life contained the whole problem of poetry and the inner life in America.” Yes, the inner life is hard when road salt is eating your hatchback. Every Bellow novel is about that. Maybe every Midwest life is about that.

I thought about this as I sipped my Central Waters Mud Puppy Porter at an arcade bar called Emporium in Wicker Park, waiting for the hairstylist to finish shopping at the vintage stores. There were 41 different classic arcade games lining the walls of the place. It was full us, full of the boy men in our practiced plaids and the girl women in their cigarette jeans.

Earlier in the day we’d gone for Americanos at a coffeeshop up the street called The Wormholethat was completely decorated with 1980s pop culture artifacts. There were movie posters on the walls and a cabinet tv set up with couches where you could play NES games. Above the washrooms in the back was a Delorean. Yes, the Back to the Future Delorean. Back to the future seemed to be a theme for Wicker Park, so savvy in its targeting of my nostalgia centers.

The hairstylist grapples with things in The Wormholest
The hairstylist grapples with things in The Wormhole.

I came out of the bar with my fist full of ones. Chicago has fewer loonies than Winnipeg, which is a problem. Eating and drinking in Chicago leaves you with so many ones. American money! Nothing else feels like it. Nothing else feels so much like money. The bills are slick with the essential oils of a hundred thousand wanting hands, the greases of so many greedy mitts, the phantasmagoria of so many desiring souls. So many ones. So many ones.

Walking to the transit station with a gut full of designer taco I looked up at a large billboard above Milwaukee Street that said “Hey interesting people: go make babies”. You might think this is a campaign by some Christian organization seeking to jar us hedonists out of our cult of the self, but it’s actually NPR. They want more listeners. My adult female traveling companion and I caught the train back to our place where we did nothing whatsoever that even comes close to resulting in new NPR listeners.

After a week in Winnipeg’s southern emulator I had only crossed off a quarter of my Chicago to-do. Still staring up at me from the list were not insignificant entries like “take tour of the Frank Lloyd Wright House and Studio”, “See the Ukrainian Institute of Modern Art”, and “Fix an election”. But we rolled quietly out of Pilsen early on Sunday morning and pointed the narrow nose of the compact car north.

Is Chi-town worthy of being the southern you-know-where? I don’t know. Yes, Chicago is a lot like Winnipeg, but with everything turned down to about a 4 or a 5. The colours are all a little more vivid and exact, leaving you wanting for our breathlessly pale renderings. The bars and the coffee shops are a little too conceptually bang on, leaving you with little to yearn for in your pestilent prairie heart. Everything’s just a little over-ripe.

As the skyline retreated from me in the rearview mirror I decided that Chicago may be the “Winnipeg of the South” but it was high time for me to get back to the real thing.


Ross McCannell is a writer and tree-planter. He winters in Winnipeg. Follow him on Twitter @RossMcCannell.