Chicago as a holding room: Making the most of a twelve-hour layover.

“I give you Chicago. It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitling and sparerib. It is alive from snout to tail.”

— H. L. Mencken

Chicago will forever be Paris to my parents.

“We’ll always have Chicago,” I imagine them saying to each other. Their obsession with the Windy City began more than ten years ago, when my father started going there for an annual business conference. After his first lonely trip, my mother began to accompany him and the rest, as they say, is history.

I didn’t have the chance to visit Chicago until I was twenty-one, but the city had long before taken on mythical qualities to our family. Every year, my parents returned home like different people, even after just four or so days away. Every year, we seemed to hear the same stories of breakfast at Ceres in the Chicago Mercantile Exchange building, the view from the top of the Sears Tower, and long walks back to the hotel after dinner at their favourite Italian restaurant.

I always wondered if Chicago wasn’t one of the secrets to their marriage.

Over three years would pass before I returned to the Windy City, this time for a mere twelve hours. I landed in Chicago this past Monday night, as the result of a serious travel booking mishap. Rather than whiling the hours away in the airport, desperately trying to achieve some measure of sleep all while keeping a vigilant hold on my bags and purse, I decided to book a hotel room. A few hours of sleep, a shower, and free breakfast the next morning seemed just the thing to ready me for the flight to London. My summer job with a major hotel chain still held some perks and I was able to secure a bed for the night at the same rate I’m used to paying for a cheap bunk in a hostel dorm.

From my seat on the shuttle on the way to the hotel, I could see a sign over the highway featuring a picture of the city’s skyline and the words, “Welcome to Chicago.” We took a different route, though, going not in the direction of downtown but to a stretch of road lined with airport hotels and overnight parking lots. Moments earlier, just before landing, our flight attendant had directed our gaze to the left side of the plane, from where we could see the heart of Chicago, its cluster of skyscrapers and towers, lit up among a grid of orange horizontal lines.

“It always reminds of something medieval. It just looks special to me,” she said in the drawl I’d grown used to over the flight and I thought of how she, as an employee on a regional airline (for eight years, I overheard her telling another passenger), must pass over this spot a thousand times a year and yet never tire of it. Sometimes, all you need from a city is a bit of skyline, a few trees along the road still glowing with Christmas lights, and the memories and associations that place can conjure up in you.

At the hotel desk, the receptionist informed me that they had given me an upgrade since I was an employee. A small twinge of guilt passed through me, but quickly faded after I saw my room. I’d spent the last two weeks sleeping in my sister’s bedroom, giving her my infinitely more comfortable bed in hopes that it would speed up her recovery after brain surgery. Now, before me in Chicago, was a king-sized bed that seemed to stretch on into eternity. It almost seemed too good to be true.

When I’m home, I find it hard to pull myself away from family and friends, feeling bad about wasting precious time holed away in my own room when I could be downstairs. Sometimes this doesn’t end well; my need, as a tried-and-true introvert, for a bit of space now and then never being met. But this room, with its tidy, clean hotel air, designer couch and lounge area, and clever dispensers of shampoo and soap in the spacious shower, was just what I needed.

And so as I settled in for the night, I thought less of the inconvenience of this purposeless stay in a city I won’t even get to see, and more of the way my time in Chicago would function as a holding room, a place to process and transition back into my life in London.

If only I’d had more time to sleep in the next morning…