Reflecting on 20 Years in Chicago

I looked over the top of the Merchandise Mart at the Sears Tower and smelled chocolate. I could hear the Brown Line seventeen floors below me. It was a new sound, one I’d quickly get used to, just like I’d get used to the idea that a city could smell like chocolate.

I was alone, and knew that even though I was in the middle of thousands, I didn’t know a single person.

I was home.

Twenty years ago today I moved to Chicago. It was an impulse decision that was a long time in the making. I’d known for some time that I needed to move so I could be closer to my son, but I didn’t want to make the leap. It was scary, the idea of picking up everything and moving to a whole new place. I was single for the first time in my adult life, had just gotten my degree in journalism, and had a wonderful circle of friends. I hemmed. I hawed.

Then 9/11. 

I drove up to Chicago on September 15, signed a lease September 16, calling my parents, who lived in Lisle, on my way back to Indianapolis to tell them. I moved to my deluxe apartment in the sky October 20.

Twenty years ago, today.

A caravan of ten drove north on I-65. As we unloaded, Binny’s delivered beer. What? A liquor store that delivered? What is this, Heaven?

No, Theresa, it’s Chicago.

I didn’t have a job, but Kinzie Chophouse hired me two days later, and they guaranteed I’d have off the two weekends a month as well as any holidays I’d get to see my son. I could see the back door of the restaurant from my living room window. I could also see the lake, if I peered from the half-bay in my bedroom.

My first few months were all about acclimation. Acclimation to waiting tables again, acclimation to a new city, acclimation to solitude, and acclimation to the knowledge that I could hop in the car and see my son in an hour and a half (two on Fridays) instead of four.

I could have moved to the suburbs, but I wanted to give both him and me new experiences. I intentionally chose that apartment because it had a view of the Sears Tower. It was my “don’t let the bastards win” middle finger to the terrorists.

Two weekends a month I’d drive to the suburbs, pick up my son, and bring him to River North. We’d spend the weekend exploring. He loved my new place. Called it a hotel, because with a doorman and luggage racks and a convenience store on the first floor, it certainly seemed like a hotel. We even had a half-acre park, a fitness center, and a pool. 

How could I not fall in love with Chicago?

The Riverwalk didn’t exist. Millennium Park didn’t exist. Hudson’s and the Ohio Street Coffee Shop and the Sun-Times building, low slung among the skyscrapers, did. We’d walk to see the river dyed green. Yep, it’s green, let’s go, he’d say. He wasn’t too impressed then, but it’s a fond memory now. We’d walk to Ohio Street Beach, to Grant Park, to Navy Pier. We took the train to Wrigley for a game, but it was so cold we decided to take the train back and I made ballpark-style nachos and we watched the Cubs while curled up in a blanket.

The rest of the time, I worked and learned everything I could about this magical place I called home. I met a man who became my “Chicago sherpa,” a wonderful friend who regaled me with stories of the city’s past. We lost touch years ago, but his influence led me to create The Local Tourist.

It was February of 2002 when I launched my new guide to my new neighborhood, and it consumed me. I continued to wait tables and, as one does when one works in the industry, would go to the bar next door after my shift.

My coworkers – my new friends – and I would talk, sometimes about patrons, good and bad, but most of the time about other things. I’d get up early each day and work on my site. Writing, learning everything I could about internet marketing, faxing (yes, faxing) businesses I included in my newsletter and on the site. On nights I wasn’t working, I’d attend networking events.

I slept very little. I made very little money. But I knew that The Local Tourist was it – this was my dream, my job, my dream job.

After a few years downtown I moved to Lakeview East. Now I could walk to Lincoln Park Zoo and Wrigley Field, and I’d run on the lakefront path. My son and I would pick up bento boxes at New Tokyo and burgers at Wilde. Pastoral was down the street.

Was this Heaven? No, Theresa, it’s Chicago.

(Forgive me for the repeated trope – I was at the Field of Dreams movie site a couple weeks ago.)

After a brief stint in Humboldt Park, I ended up in Logan Square for several years. I met Jim. He moved in. We’d walk around Palmer Square. I’d hop the blue line and be downtown in fifteen minutes. Revolution Brewing opened. So did Cafe Mustache. Then a second location for Chicago Diner, whose vegan options made my lactose-intolerant mom very, very happy.

In 2014, my time in Chicago ended. Logan Square was h-o-t, and our landlord increased the rent by 46%. By this time my son was in college, so Jim and I put everything in storage and traveled for six months before moving to Elgin. We did staycations and road trips and camped, a lot, and a team of contributors helped keep the Chicago content going.

Jim and I married in 2015, and in 2017 I fulfilled a dream I’d had for as long as I could remember: I wrote a book. Since then I’ve written two more and contributed to a third. My most recent book is a love letter to Chicago. It was borne from an idea planted by my Chicago sherpa two decades ago.

While I don’t live in Chicago any more, and haven’t for seven years, it still has my heart. It will always have my heart. Chicago is where I found myself. It’s where I found my passion and it’s where I found my love. It’s where my son and I developed a deep and abiding relationship. 

I’ve spent those twenty years creating memories, not just my own, but also for others. I’ve hosted nearly a hundred events: Chef’s Tables, which showcase restaurants in an intimate setting, and AlphaBeer, an insanely fun focus on craft beer, one for every letter of the alphabet. I had my own restaurant week and showcased the photos of hundreds with 100 Days of Chicago. I’ve raced – and been thrown by – a camel, flown with Lima Lima and Aeroshell above Lake Michigan, kissed the Stanley Cup and interviewed Harold Ramis and Jacqueline Smith and many more. I’ve seen and done things I never imagined when I signed that lease.

I made a lot of mistakes, especially in the beginning, but don’t we all?

One of those mistakes is fairly recent. In the panic of March 2020, I moved all the Chicago content from the last nineteen years to Your Chicago Guide. The concept made sense to me, but what that move meant was that the site inspired by Chicago no longer has Chicago in it.

I’m fixing that. In addition to my stories about places across the country, I’m going to incorporate, and re-incorporate, the city that started it all.

When I moved to Illinois and Franklin, all I had were hopes. I knew I wanted to write, and I knew I wanted to write for myself. I believed that because I was doing the right thing, for the right reasons, I’d figure out how to make that happen. It took me some time, but I did, and now I get to go places and write about them. That’s my job.

And I owe it all to a place that smells like chocolate.