My kind of town, Chicago is.
When I was a kid, Chicago symbolized The Big City. I was very much aware that my hometown was, in baseball terms, a Triple-A locale — the minor leagues. Kansas City, just down the road, had a big league club. But Chicago had two of them, and it didn’t seem as exotic as, say, New York or LA. If you had asked me at any point from roughly age 8 to 20 where I wanted to live, I would’ve said Chicago — there were great museums, public transportation, and it was huge. It pulsed with energy. And when I was there, I did, too.
So with this week’s Democratic National Convention in Chicago, it seemed like a good time to re-visit the Windy City, the Second City, the City of Broad Shoulders. But since the kids are in school, the travel budget’s tight, and I gotta work, let’s make this visit via memory lane.
Here, a few scenes from my many trips to Chicago:
Summer 1990
My age: 9
Percentage of my time at that age spent thinking about skyscrapers in general, and the Sears Tower in particular: Not 0
Floors in the Sears Tower: 110
Windows in the Sears Tower: 16,100
Tears I cried when my parents didn’t wake me up to see those windows lit up at night as we drove into Chicago: Countless
Year that Comiskey Park opened: 1910
Saves Bobby Thigpen earns in 1990 for the Chicago White Sox: 57
Single season record for saves as of the end of that season: 57
Number of those saves I witness in person…: 1
… Followed by how many fireworks launched from the famous “exploding scoreboard”: A lot
Years Comiskey Park was open after that season: 0
Spring 1998
My age: 17
Percentage of my time at that age spent thinking about Radiohead’s opus OK Computer: At least 80
Number of concerts Radiohead played during my visit: 1
When I realized Radiohead was playing Chicago during my visit: The morning after the show
Songs Radiohead played: 20
Percentage of those songs that are still pretty awesome: 95 (Sorry, “Lurgee”)
Cubs games I attended on that trip: 1
Members of my family allowed onto the field before that game: 1
Percentage of those members who were me: 0
Number of players and coaches my Mom met while walking the bases of historic Wrigley Field: Quite a few, as I remember it
Number of kids from my high school who married into the family that now owns the Cubs: 1
Number of free tickets I have received as a result: 0
May 2001
My age: 20
U2 concerts I attend on this trip: 1
Hours my friend and I spend in the GA line before the concert: 8? 10?
When I realized our tickets are not, in fact, the GA tickets I requested, but are seated in the nosebleed section: Not soon enough
How long before the show I had bought these tickets: At least six months
What the teen behind the counter of the Ticketmaster booth in Omaha said when I asked to buy U2 tickets: “How do you spell that?”
When I should have started to worry: Right then and there
What I decided to do after I realized our tickets were not for the GA section — which, I should add, is right next to the stage, and even inside the stage, thanks to the Elevation Tour’s innovative heart-shaped design: Just roll with it
How long the ticket-taker debated what to do when he took our tickets: About three seconds
My heart rate during those three seconds: Off the charts
What he ended up doing: Letting us go to GA
How long my gratitude toward that kindly ticket-taker has lasted: 23 years and counting
Rows of people between us and Bono: 1
Number of those people with a truly majestic mullet: 1
Number of times Bono suppressed a laugh upon spying said mullet: At least once
And how long it took for him to notice the aforementioned hairstyle: About two minutes into the opener (“Elevation”)
Number of times you can hear me yelling “Happy birthday, Bono” on a bootleg of the show I used to have: At least once
July 2006
My age: 25
Pitchfork Music Festivals attended: 1 (the first!)
Artists who performed on the main two stages: 22
Number of artists whose sets I really remember: 7ish?
Number of those artists who were The National: 1
Number of times I’ve seen The National: At least 4
Number of times I’ve seen The National on purpose: 0
Number of times I would like to see The National again: 0
Number of those artists who are Jens Lekman: 1
Number of times I’ve seen Jens Lekman: 1
Number of times I would like to see Jens Lekman again: More than 0
Number of Cubs games I attended on this trip: 1
Cub games watched from the famous rooftops beyond the outfield: 1
Number of times I would do it again: 1 or 2
Degrees Fahrenheit on the rooftop that afternoon: If I had to guess, at least a million
Innings pitched by Cubs legend Greg Maddux that day: 6
Innings pitched in a Cubs uniform by Cubs legend Greg Maddux after that day: 0
Amount of applause for Maddux as he walked off the mound: Lots
September 2022
My age: Let’s stop including this, shall we?
Number of kids with me: 2 (my own)
Amount of time we spent on Navy Pier this trip: Probably too much
What do you mean? Like, how many times did you eat at Harry Carey’s?: Twice
Oh. But life changes when you have kids, right? And besides, it’s really not that bad — solid burger — just a little more than you’d want to pay, and maybe not as “authentic” as some of the other spots where you could’ve eaten. And it’s next door to the children’s museum. Right?: Right!
And besides, you rode the Ferris wheel there, and that was pretty magical, even when it got a little rainy: Absolutely
Floors in the Willis Tower: 110
Windows in the Willis Tower: 16,100
Tears me and the kids cry when the weather suddenly turns rainy, which means we will not be going to the top of the Willis Tower as planned: 0
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Ultimately, I overshot things and ended up in New York after college, which is another story for another time. But I never stopped loving Chicago. And if I close my eyes, this playlist1 takes me there — to riding the El, to shopping at Jazz Record Mart and buying B.B. King and Liz Phair CDs for the drive home, to concerts and ballgames and friends and family. And to the first time I visited on my own, when I made sure to make an evening tour of Lake Shore Drive, and took in the country’s biggest skyscraper in all its nighttime glory.
“Via Chicago,” Jeff Tweedy
I mean: Why fight the obvious? I’m partial to this vulnerable and lived-in version from an album of solo re-recordings of Wilco songs. Incidentally, it’s been 25 years to the week since the first time I saw Wilco, when they opened for R.E.M. at an amphitheater outside St. Louis. I couldn’t have imagined then that, a quarter of a century later, I’d still find meaning in their work (new and old), and I’m grateful for that journey together. Still haven’t seen them in Chicago, though!
“Tonite Reprise,” The Smashing Pumpkins
Again, no points for originality, but I’m fond of this charming alternate version of the Pumpkins’ mega-smash. The lyrics are a little different — here, it’s “my” city by the lake, rather than yours — and, dare I say, a little better? Fun fact: Billy’s voice is shot in this recording because he had just come back from a Bulls playoff loss to the Orlando Magic.
“Chicago (Demo),” Sufjan Stevens
1. I vastly prefer Sufjan’s sparer arrangements to the ultra-ornate sound he introduced with the Illinoise record, so once again, we’re going with an alternate version of an obvious pick.
2. I had never noticed how much the opening riff sounds like “Tonight, Tonight.” I gotta think that’s intentional.
3. Well, I’ve made it this far without mentioning The Bear, the best (also: only) show I’ve watched in the past few years. Suffice it to say that the opening montage of season 1, episode 7 — aka the one that’s otherwise one continuous take — is some of my favorite visual storytelling ever, and captures Chicago in all its beauty and glory and grit. It also re-introduced me to this version of this song. R.I.P., Lin Brehmer.
“Chicago at Night,” Spoon
A slinky love letter from Austin.
“Pulaski,” Andrew Bird
Take it from me, Britt Daniel and now Andrew Bird: There’s something about Chicago at night.
“Chicago,” Japandroids
A new entry to the canon. Excuse the profanity!
“The El,” Rhett Miller
An exuberant love letter from Austin.
“Windy City,” Alison Krauss > “In the Ghetto,” Dolly Parton > “The Sidewalks of Chicago,” Merle Haggard & The Strangers > “Rogers Park,” Justin Townes Earle > “Chicago Promenade,” Jason Isbell
Welcome to the portion of our playlist that portrays Chicago as scary and/or desolate, particularly for those arriving from a small town.
“Lake Shore Drive,” Aliotta Haynes Jeremiah
But now, back to the city’s seductive qualities, with a rollicking tribute to the city’s scenic artery.
“Southside Chicago,” Otis Brown
A swingin’ place indeed.
“Chicago,” Tom Waits
I wasn’t previously familiar with this song, and so I wondered what I wonder whenever hearing a new-to-me Tom Waits song: Will this be the sentimental, closing time at the corner bar Tom Waits? Or will this be crazy Tom Waits? Well, it turns out this is one of his tunes that hit the sweet spot, the overlap of that Venn diagram.
“Jesus Just Left Chicago,” ZZ Top
A raucous love letter from Houston.
“Chicago Seemed Tired Last Night,” The Hold Steady
Not this week, it didn’t.
“Meet Me in Chicago,” Buddy Guy
Sure, the lyrics of this song are extremely pandering, but you can’t deny the guitar.
“Take Me Back to Chicago,” Chicago
And now, a song about Chicago by the band Chicago (from Chicago).
“Chicago,” The Doobie Brothers
A bluesy trifle from the pre-Michael McDonald era.
“Sweet Home Chicago,” Robert Johnson
Of course.
“Chicago Blues,” Jimmy Rogers
Perhaps you’ve heard: Chicago has been home to some outstanding blues artists over the years. This is one of them.
“Born in Chicago,” The Paul Butterfield Blues Band
And another one.
“2120 South Michigan Avenue,” The Rolling Stones
Not one of them, but I feel like they’ve earned honorary status. The title refers to the address for Chess records, where they laid down this instrumental track.
“Via Chicago (Live),” Wilco
And now we’re back where we started, with an electric live version from the band’s current lineup, one that replicates the experience of walking around the Windy City.
Jeff Tweedy: “[“Via Chicago”] was an effort to try and re-create the sensation of walking underneath the L tracks. Basically, trying to have a conversation with someone you’re walking with and having it be completely destroyed or undermined by this brutal noise. I don’t think we did a good job of it [on the album], actually. I think we got better at doing it live.”
Searching for a home,
P.L.U.
Obligatory disclaimer: This playlist omits “Chicago” by Graham Nash, the jazz standards “Chicago” and “My Kind of Town” (I’m guessing you’ve heard them), songs from the musical Chicago, and much of anything that reflects Chi-City’s massive hip-hop, pop-punk/emo and house music scenes. My apologies to the late Frankie Knuckles.
Fantastic.