Three Days in Chicago

When I showed up in Chicago, the only plan I had was to improvise. Like an actor in a Second City improv show, I had a vague idea what I was getting into, and my intention was to simply go with the flow and see where Chicago took me. I ended up coming away with an appreciation for the contrasting high-brow/low-brow experiences the city had to offer.


No sooner had I arrived at my friend’s home in Wicker Park we were heading downtown to visit the sprawling Art Institute of Chicago. I easily could spend an entire day browsing the collections– the iconic American Gothic, urban darkness of Night Hawks, the dizzying pointellism of Seurat’s A Sunday Afternoon on the Island of La Grande Jatte– not to mention the disturbing, intense energy of Balthus’ Girl and Cat, Van Gogh’s colourful bedroom portrait and the imposing yet ethereal Sky Above Clouds IV by Georgia O’Keefe, calling to mind the endless stretch of pale pink sunrise I had glimpsed from the plane window on the flight there.

The early flight had left me tired however, and after a thoroughly enjoyable and unpretentious plate of tacos at a nearby taqueria, it was off to bed.


The next morning we continued the Mexican theme with brunch at Dove’s Luncheonette, a lively counter seating-only spot with a soul and blues soundtrack and tex mex-inspired menu. It was rather hectic sipping coffee elbow to elbow with our dining neighbours but I left with a new love for chile rellenos.

We wandered down Milwaukee, ducking into trendy boutiques and overstuffed used bookstores, and I couldn’t resist trying out a few of the pinball machines at the cavernous Emporium Arcade Bar. There were local beers on tap and the unbelievable lineup of old arcade and pinball machines was only 25 cents a play. I could have spent all day there sampling craft brews and trying to master multi-ball mode on Theatre of Magic.

My friend was nice enough to take me back downtown so I could visit a few clothing stores we lack at home in Canada and we took the opportunity to walk down the Magnificent Mile, undoubtably named for the looming skyscrapers and historic towers that line the street. There’s a fantastic mix of architecture in this area, a result of the catastrophic fire that scorched the city to a blank slate in 1871. The sidewalks are thick with tourists and shopping locals alike crowding the entrances to ritzy retailers, so take care if you’re stopping to admire the Hancock building or the unmistakable cob towers of Marina City. We ended our walk at Millennium Park, unable to resist the draw of Cloud Gate’s reflective surface. The “bean” seems to bring to visitors great delight– I love seeing people interact so enthusiastically with public art.

Back in Wicker Park, we stopped in at the delightful dive Rainbo Club for a bracingly strong gin and tonic (bless America’s free pouring bartenders) and then headed to Pequods so I could try deep dish pizza. The crust was fluffy and sweet, the sauce thick and the Italian sausage plump and zesty– one slice was a filling meal in itself. The menu boasted of cast iron pans seasoned for more than a decade, giving the tall crust its tantalizing caramelized crispiness.

There was a stop at Goose Island Brewery for a strong, hoppy pint of the Illinois and we ended up at another dive bar, where the PBRs was cheap, the music loud and enough kitsch lined the wall to keep me smiling for the rest of the night.


Saturday morning my friend and I were gratefully clutching cups of coffee over a lox bagel and vegan biscuits and gravy at the raucous West Town Bakery & Diner. I went back downtown with the mind to see Lake Michigan and where the blue sky day would take me. It was nice to wander on my own down the empty side streets, watching the shadows play through the wrought iron tracks of the L train, clattering over my head and snaking through the skyscrapers on its elevated path. I briefly considered visiting the Sky Deck of the Willis Tower but the sight of the massive line up of tourists snaking around the block and thought of the ensuing crowded elevator ride to the top shook me of that notion. (A missed opportunity: the Signature Lounge on the 95th floor of the Hancock building.)

Lake Michigan was a pretty shade of turquoise, and taken with the beautiful (but predictably blustery) weather I rented a Divvy bike and rode along the lake shore. To be honest, coming from a place where the trails are integrated with the landscape so seamlessly, the broken concrete and adjacent busy highway seemed a bit of a sad counterpart to the sparkling lake waters. I could, however, see the appeal of the sandy beaches on a hot day, swimming with the towers of Chicago as backdrop.

The evening found us starting things out with Old Fashioneds at The Green Mill. A dimly lit cocktail lounge with more than 100 years of history, it’s probably best known as a prohibition-era hangout for gangsters, including Al Capone. That night the only unsavoury thing going down in the green vinyl booths were the shots of the bitter wormwood liquor Malört being distributed. Malört is infamous in that it’s vile and made locally in Chicago, so be sure to imbibe if you’re in town.


As I blearily mashed my face deeper into the top of my backpack on the train to meet up with my Chicago-based family, I couldn’t help but wonder when during the previous night I had tapped into the magic algorithm that had blessed me with such a nuclear hangover. Had it been the much maligned Malört? The Ethiopian honey wine (and who even knew such a thing existed!)? Or perhaps the enormous bottles of Polish Żywiec beer? It had been impossible to keep count of how many I had downed at Alice’s, a bar otherwise unremarkable but for its droll karaoke host and amazing song selection. Perhaps I had just been intoxicated with too much joy singing Gypsies, Tramps and Thieves into the crowd while the host waved a Canadian flag seemingly conjured out of thin air.

Luckily the Chicago family had a good sense of humour about my condition, and after a pleasant visit, I found myself in a car heading down the (apparently always under construction) Dan Ryan Expressway, the iconic city skyline gleaming in the distance in the red-gold light of the setting sun. It was one of those travel moments where, suddenly seeing everything from a new perspective, alights something in your mind.

A-ha, you think. I’m somewhere different than usual.

I was back in British Columbia by Monday afternoon and couldn’t help but notice the stark contrast of the lush west coast greenery to the urban concrete and brown brick palette of Chicago. It was refreshing to dip my toe into the friendly energy of the midwest metropolis. Three days was enough to take in everything from classic art to classic dives and I can’t help but love a place where I can have a little bit of everything. However, next time I’m declining the Malört.






1 Comment

  • Reply January 29, 2016

    Travel Guide

    “Bizarre travel plans are dancing lessons from God.” – Kurt Vonnegut

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