Beyond “Second City”: A New Yorker Moves to Chicago

This piece was originally published in the February 14, 2016 edition of Write City Magazine, the magazine of the Chicago Writers Association.

After living in New York City for 26 years, I got a dream job in Chicago I simply couldn’t turn down.  I wasn’t sure what the move would entail—my initial associations with Chicago having to do with Al Capone, the Bears, house music—but some preliminary Google searching assured me that Chicago was simply a “smaller, cleaner, friendlier version of New York.”

Across the blogosphere Chicagoans compared their city to New York on nearly every level, from neighborhoods—Pilsen, the new Williamsburg—to amenities—if you like Per Se, youll love Alinea.  Deeper Web searching yielded even bolder claims to the ways “Chicago is infinity times better than NYC,” “kicking New York’s ass.”  These claims rested on the premise that Chicago offers pretty much everything NYC does but without all the stressors.  Or as one blogger put it, it’s “NYC Lite.”  What New Yorker wouldn’t love the Big Apple scaled to size and rendered livable?

My first week in Chicago, I was eager and ready to take a bite out of this new apple.  Back at home, I’d loved cocktail lounges with a secretive feel, so I sniffed out Chicago’s parallels. But things here immediately began to go wrong.  Showing up at the doorstep of one such lounge left me bewildered: Why were they letting absolutely everyone in? Why were they closing so early?  Where was the concept fashion?  Where was this, where was that?  A wall of differences between the two cities pressed in on me day after day, week after week, regarding nearly every aspect of Chicago life.

Continued let-downs left me deflated.  One full year here, I set out at 11pm one evening, as I used to back in NYC, for a few hours of late-night midsummer strolling across bustling urban landscape.  40 minutes in, thats it, I stopped short on a corner.  I was done.  As beside me a Chicagoan beamed with pride before his downtown Chicago skyline, I hissed, Its not New York, and cabbed back home to bed.

Why couldn’t I just experience Chicago on its own terms, allowing its charms to irradiate my mind and imagination as New York once had?  The charms were all there before me: why couldn’t I let them shine in?  I think that on a ground level I was, as if seeking a former love in the arms of a new acquaintance, still looking for New York.  And I think that this expectation arose precisely from the claims I’d encountered concerning Chicago as a “smaller, friendlier, cleaner version of New York.”  Having lived here for six years, I’d argue that the most apparent similarities between the two cities—“skyline, architecture, food, setting”—eclipse precisely the things that make Chicago so wondrously unique. What’s truly here in the guts and soul of this city, and where might we find it beyond the shadow of “Second City”?

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In 2010,  I prepare to attend a downtown Manhattan soiree.  There will be a New York Times music critic as well as a Booker Prize-nominated writer in tow, so I spend previous weeks frantically researching music charts and poring through as many book reviews as I can cram into late nights.

Arriving at the party at midnight, I rock up the industrial elevator shaft and step out into the loft, model on my arm.  We are the first people there, and, feeling naked now despite the low lighting, I jolt my date into conversation.  As at around 1 AM a crowd starts forming, the music critic and novelist finally appear among the socializing faces. We get within enough proximity to one another to broach conversation.  One of them invokes an esoteric music album, and I stutter: “Oh yes, that—that—1992 sophomore album was transcendent!”

And now the writer: Had I read that novel that hits stands next week?

“Of course I’ve read it already.  Who hasn’t?  Simply transcendent!”

Suspecting fraud, he presses me, quoting his favorite lines.  I nod.  I nod.  Can he smell the dew swelling under my collar?  “Sublime; yes, s—sublime.”

He asks my thoughts on an obscure plot detail.  I stammer incoherently.  He bores his gaze into me.  A beat, then he’s away.

Now I am at a soiree in Chicago in 2015.  The evening is to celebrate a Hyde Park intellectual who until last year had his own radio show on NPR. Chicago intelligentsia, denizens of the art world, create buzz about the room.  As at around 9 PM the guest of honor approaches to shake my hand, I frantically call to mind the archived radio shows I’d studied the entire previous week in preparation.  He preempts me with a smile: “Hey I heard you got that article published on education and race—congratulations!  I’m looking forward to reading it!”

Is he mocking me?

I hesitate, but find something curious happening.  A doorway opening; a space emerging to talk about the writing life.  Its struggles, its realities.  He offers lucid advice, without judgement.  We gab on easily about our children, his life after NPR, and the church we both began attending last year.  I feel a thaw taking place in the air about me.  A moment of wit and a burst of laugher and—for just a second—I forget where I am.

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In 1952, A.J. Liebling unleashed a haunting spirit upon Chicago, naming it “Second City” and fating it to wrestle with the idea of “New York” as the looming standard against which it is judged.  Chicago defends itself from such “savage” criticisms, insisting on the ways in which NYC remains dirty, rude, nasty, snobby, unaffordable.  Meanwhile, New York glances back with raised brow, responding, as Rachel Shtier did in her 2013 New York Times article, with chilling laughter.  It becomes a never-ending co-dependent relationship.

But zooming out, one finds the greatest American cities asserting their identity without anxious preoccupation with other cities: Portland’s hipster quirk, Charleston’s southern charm, Nashville’s country music, Louisville’s barreled whiskey, Miami’s beach glam. What about Chicago?  Just another, “smaller” and “cleaner,” New York?  How might we envision this city apart from the long hard shadows cast from the coasts, empowering it to emerge beyond “Second City” and “Third Coast” into its true identity as our country’s spiritual center?

I myself am beginning to put my finger on the pulse of it—this that Chicago has yet to name for itself and live into—and I must admit I’m beginning to fall in love.

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Erick Sierra

Erick Sierra

Erick Sierra lives in Pilsen, Chicago. Visit his website at