Chicago in Times of Trouble
Ready to throw bricks, but too overwhelmed to leave the house.
Early September makes me antsy.
Maybe it’s leftovers from years of starting school at this time of year. Or the disconnect that comes from seeing the push for autumn while living in a place that hasn’t had an autumnal September since 1991. I was a freshman in college, and my parents had to get sweatshirts and sweaters to me because it suddenly got cold on the first day of autumn. During the first week of November that same year, I took a spontaneous evening walk in the snow with a nice young man. That never happens anymore, either.
I want to be out. I want to be somewhere. But I don’t want to leave my house. It looks exhausting out there.
With Chicago in the news, I woke up this morning thinking about jumping into my car and just going. It’s less than a five-hour drive. I could be arriving right now, in time for a late lunch before maybe throwing some bricks at some tanks.
It’s been years since I’ve gone this long without a Chicago trip. I haven’t been since late May of 2024, when it rained all three days I was there, causing a migraine that kept me inside for the duration of my stay.
Have you ever gone to a place, stayed for a brief time, but a moment from the trip imprints on your memory, to the point that the experience becomes the gold standard? It’s never the moments I anticipate—the big events or special occasions. It’s in the feel, sounds, tastes, and mood, all colliding in a moment to never be captured again.
Chicago in September feels like sitting in front of the fire at the Fairgrounds Coffee location that used to be in Wicker Park, after attempting to sit outside. Even though the temperature was in the 60s, it was frigid because of the wind off the lake. The briskness and bite of the air, the rush of traffic, coffee aroma, gleaming sun in a bright blue summer sky, and the rush of blood into my cold flesh while I scribbled some words in a notebook by the little fireplace. That’s September in Chicago for me.
The trip was a Covid lockdown-era anomaly. Jeff Tweedy was playing a one-off socially distanced concert at a drive-in theater in the outer suburbs. Starved for live music for six months, of course I made the trip. I had bought my little SUV a few weeks prior, and my friend Anne (Ann? I can’t remember because my brain always turns her name to Anodyne) co-piloted. While we waited in the line of cars, we got news that Ruth Bader Ginsburg had died. So it was September 18th, and we knew we were going to be fucked for a few years, minimum.
We did not predict that, in just under five years, Chicago might be under attack by the American government. How bad can it get? Well, here we are.
The show was therapeutic, despite the isolation of everyone being at their cars instead of mingling and hugging like we all do at Wilco/Jeff Tweedy shows. When he played Pop Staples’ “Friendship,” I just about buckled from the loneliness and disconnection brought on by the pandemic. Being with a friend and reminded of what that means was akin to getting the bends from swimming to the surface too fast.
Has everything felt a little like that since March 2020? Just me?
We spent the night in the ‘burbs and, even though we needed to return to St. Louis the next day, we took the time for Superdawg and a jaunt into Chicago proper. Anne had relocated from Chicago to St. Louis a few months prior and wanted to touch base with some friends. Not wanting to impose, I offered to drop her off while I headed to Wicker Park and Fairgrounds. Where the sensory palette of the moment forever defined what a Chicago September is.
I’m not driving to Chicago today. Not from fear—I would love to be there, for brick-throwing purposes and for Chicago in September purposes. But I do have a sense of self-preservation, along with a tight budget. I’ll be in Los Angeles in 2.5 weeks. Then New Orleans for my birthday in October (I talked myself into it with my Katrina post). And then Monterey in November, with a long weekend in Kansas City with the kid somewhere in between it all.
And there are two brief Chicago trips. Late autumn/early winter ones. I’m seeing Golden Smog in December and Patti Smith in November. A band I didn’t think I’d get to see again, and a celebration of the 50th anniversary of one of my favorite albums (Patti’s Horses), all with winter coats and frosted breath, bracing against the wind off Lake Michigan, imprinting me yet again with the essence of one of the greatest cities in the world, that I’m lucky enough to have nearly in my backyard even though I've perhaps taken that closeness for granted in the last year.
Let Chicago be the place where this regime gets the chips in their armour that let in a cold that will never leave their bones.
Buy me a coffee for my next visit to Fairgrounds (or Dark Matter or Intelligentsia or Metropolis or Big Shoulders or …)