Menu Home

Why I’ve Stayed in Chicago for 20 Years

The turn of spring to summer is my dual Chicago anniversary. I’ve written this blog for 18 years. And I’ve lived in my adopted City of Chicago for 20.

As I told StoryCorps years ago, Chicago happened for me because of 9/11. As I’ve now known since 2020, running away from my native New York City was really an attempt at escaping my then-unknown autistic anxiety.

A decade ago, on my tenth Chicago-versary, I retold the story of visiting here six times in three months in early 2003, then being guided by my now-international Media Goddess friend, Sarah, “New York will always be there, but if you don’t give Chicago a try, you’ll never know.”

It’s been quite the ride so far—with those last two words being particularly weasely. I thought I ’d only be here a couple of years, but even with all of this city’s post-Lightfoot/post-pandemic problems (and, if you’re connected with me on Facebook, my social-media bitching thereof), this stopover increasingly looks a lot more like a lifelong one.

There’s been so much happy, so much anger, and so many positive civic engagements, so much Marina City, so much transit, so much Judaism, so much Disney, so much going local, so much reconnecting since 2003. And somehow my early thirties became my early fifties.

If there’s a single post that sums up the journey and why I’m still here, it’s this one. The story of the two types of native New Yorker, told on Marina City’s 61st-floor roof deck. Most of them are too afraid of the rest of the world to ever leave the five boroughs. But some of us understand New York is nothing but the center of itself, and go looking for the world’s real center. For the past 20 years, I’ve found that center in Chicago.

For worse or better, I still do.

Five years ago in the before times, I dropped a popular piece on Quora about why Chicagoans—native or not—stay, irrespective of winter and local woes. On this side of the pandemic, in these fraught times in this battle-weary city, it’s a useful reminder to me why I’m still here. Maybe it’s a reminder you need, too. This is who we used to be here.

And I believe, for worse or better, we still are…


Speaking as a native New Yorker who has lived in Chicago for the past 15 years, I’ll put it more simply. Chicago is the city New Yorkers wish New York was, and constantly complain that it isn’t—in the same breath that they claim they “couldn’t live anywhere else.”

Chicago is cleaner everywhere, has more elbow room everywhere, everything across the board is less expensive. It’s much easier to find your way around with a far simpler and nearly universal grid system. It has cheaper, cleaner, and far more reliable public transit that never stops running in winter storms, and far cheaper and far fewer tolls.

People feel an ownership of downtown instead of feeling unincluded there. Chains haven’t taken over every local neighborhood shopping street. Amazing ethnic neighborhoods are all across the city, and aren’t punishingly crowded to visit.

Local/small-scale arts and theater still thrive here, and people get out of work on time all the time to enjoy them. Our airports (yes, even O’Hare) don’t suck and flights anywhere in the country are only 2 to 4 hours long.

We have 26 miles of almost unbroken urban parkland abutting an alarmingly enormous inland sea–that coastal critics always complain “isn’t the ocean” until they’re standing on a crowded lakefront beach in the middle of a sweltering Chicago summer with their jaws on their knees and saying silly things like, “It’s like Los Angeles!” (Literally said to me about our beaches by an Angeleno his first time here.) No, it’s like Chicago.

The local culture of niceness is like Midwest niceness on steroids. We like each other and talk to each other here as strangers all the time with no problem doing it. And because our lives aren’t inhumanely expensive, we aren’t grouchy all the time and afraid of making ends meet every month. These last two things really define the vibe of daily life here. Unlike my hometown, you don’t spend every day feeling like you’re fighting against millions of other people just to tread water. There’s a real sense of all being in it together. Our communities, from the most local and granular to the level of us all being Chicagoans, are tight that way.

That’s why we stay. That’s why we put up with government corruption and budget disasters. That’s why we stay and try to find solutions to underfunded police and fire departments, public schools, and youth summer jobs programs. It’s not easy or pretty, but life isn’t without challenge anywhere else in America either. We stay because so many things about this place make us care enough to stay. And that’s something I think outside observers ALWAYS miss about Chicago.

In 15 years, I’ve had ample opportunity to move home to NYC (including an amazing job offer) or to move on to other cities, and I’ve had my share of moments and even years of not being in love with this place. But Chicago always manages to embrace you and pull you back. Because it cares to.

As far as winters go, everybody everywhere complains about their climate, including Southern Californians and Floridians. There is always something. Before I left my New York City hometown, people complained about those allegedly mild winters every year, all winter long. Chicagoans complain like everyone else. The difference is that we don’t ever let weather stop us. We dress for the weather and go out and enjoy our city whether it’s 90° F in the heart of August or 10° F in the heart of January. That’s another thing that people who aren’t from here constantly misunderstand. We don’t huddle from our climate. We just continue to enjoy and embrace this place that embraces us back.

And, of course, the punchline is that we do all of this and experience all of this and get to have all of this in an alpha-level world city (just below the top tier of New York and London and Tokyo) with all of the cultural, and gastronomic, and educational, and economic, and international amenities that you would expect to find in a world city anywhere else on the planet. After 15 years here, I can tell you with no exaggeration that almost every “If only…” I ever heard about New York City in my more than three decades of living there as a native described something about Chicago that was missing in New York.

Which brings me back to my original point. Chicago is the city New Yorkers constantly complain that New York isn’t. Since most people asking “What is Chicago like?” questions are from big coastal cities who have never been to Chicagoland other than passing through an airport, this answer should probably resonate for a lot of people.


It definitely still resonates for me.

Categories: Backstory Blog Anniversaries CHICAGO Chicagoans

Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

My Bio | My Conversion | My Family Reunion

Follow My Socials:

Contact Me:

2 replies

Leave a comment...