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Fleeting Glimpses of Chicago

Fleeting Glimpses of Chicago

I don’t like saying I’ve “been” places if I’m literally just passing through. If I don’t have the time to really get a feel for a city or destination and find out it’s secret undercurrents, its underrated traits, it’s intimate quirks. But even though I was in Chicago for less than 24 hours, it somehow enchanted me; so I needed to write about it. 

Tired from the rumbling rhythm of the greyhound, we stepped out into air colder and harsher than I’ve ever felt. My 14kg pack felt just that little bit heavier in the aching cold, and it felt like my gloves doing nothing to protect fingers I became genuinely worried I’d lose to frostbite. 

The opening scenes of our stay in Chicago were brutal and industrial. Wide roads flowing with arctic slush were disturbed only by the occasional car, the driver peering out in curiosity at the two shivering British tourists, probably wondering what the hell we were doing out in the harsh mid-winter. 

But before long, we reached the comfort and warmth of Lou Malnati’s near our Air BnB in Soldier Field. It’s an iconic deep dish pizza joint, recommended to us by our new friends back in the Cosmos Café in Milwaukee. Unconvinced that four slices would satisfy our appetites, we ordered a large. The pizzas are so carefully crafted that they take half an hour to arrive, but boy, it was worth the wait when it did. 

The waitress flashed a knowing smile as she arrived with an enormous pan, overflowing with bubbling tomato, cheese and spiced sausage. More like a pie than a pizza, she cut deep into the centre as our mouths watered and the salty filling oozed over the soft, buttery crust. Needless to say, our eyes were bigger than our bellies and we couldn’t finish the whole thing (it did do nicely as a midnight snack later, though).

Those calories demand to be worked off, so we loaded ourselves up with our packs once again and headed back out into the whipping wind. The whole of Chicago was ours for the night; but for one night only. What do you do in a city that teases you with its atmospheric skyline and glowing streets, but punishes you with temperatures so mean they push you back inside after just a few minutes?

We opted to laugh it off. Comedy group The Second City – boasting such notable alumni as Tina Fey – were putting on a show at Up Comedy Club called Fast, Loud and Funny. It seemed as good a way as any to enjoy the delights of Chicago without contracting hypothermia in the process. 

Settling down into our seats (which were incidentally right in the centre front of the audience. I mentally prepared myself to be picked on for “audience participation”), we had no idea what to expect. The following two hours contained what was actually some of the best comedy I’ve seen in a while, blending a mix of sketch and improv. I came away with a genuine admiration for anyone who can make your stomach ache with laughter using just a random cue from the audience. 

While we’re usually not too picky about the transportation we choose, often opting to take buses, subways and metros over taxis, that night it was too cold to do anything but order an uber. It was from the back window of that car, exhausted from the journey and the laughing and the supersize pizza, that Chicago offered me one last tantalising glimpse of what makes it the favourite city of so many people we’ve spoken to in the states. 

It’s layered, winking skyline changed at every glance – towering and imposing one moment, ringed by neon blue light against a smoky, starry sky, full of old-fashioned character and intrigue the next. I couldn’t get the image of Gotham out of my head, the city exudes a dark, moody kind of charisma that I haven’t seen anywhere else. One silvery building in particular, soaring high above the others and topped with an aggressive looking steel structure and billowing smoke disappearing into the dark, looked like an ideal place from which to project the batman logo. Just saying. 

Although we only got fleeting glimpses of Chicago, they were delicious. Enough to have me singing the praises of the city along with everyone else, enough to have me planning my visit back (preferably in the summer). But it was time to move on; a flight back to Denver was waiting to take us back to Colorado, and back to the mountains. 

One of the Cool Kids in Denver

One of the Cool Kids in Denver

Brewing up a storm in Milwaukee

Brewing up a storm in Milwaukee