My Love Letter to Chicago


Dear Chicago,

I started writing this letter months ago. I knew it would take me a while to get my words just right, to best explain how I feel about you. As you read this, I’m in my car, my trunk is packed and my backseat overflowing with things I’ve collected over the past five years, I’m following Mike in his car, which is packed too, and we’re driving towards a new city and a new chapter. Although that’s partly really exciting, my problem seems to be that I’m driving away from you, Chicago. Even as we’re getting further and further apart and more and more miles and cities and then states begin to separate us, please know that I’m thinking of you and remembering the years we shared together. And, I’m sure, almost without a doubt, that I’m missing you already.

We first met when I was nineteen or twenty, I can’t remember exactly. I was in college and just visiting. It may have only been a brief encounter at the time, but you certainly left an impression on me. I can still remember how beautiful you were (and still are)—your buildings and architecture, your river and your lakefront. You were one of the most exciting cities I had ever been to. I had no idea then, that years later, we would meet again and become so close. When we did meet again, you welcomed me with open arms, just like an old friend. You promised me new adventures and opportunities. I think back to that version of myself, so carefree in comparison, in my mid-twenties, no fear of picking up, moving and starting fresh. So when Mike got a job here, we didn’t overthink it, we just went.

And, I’m so happy we did.

I wasn’t sure how long you and I would be together, so, at first, I was hesitant to love you. But, on the same page, you kind of made me earn your love, didn’t you? I felt like every time I let my guard down a little, to let you in, you would test me. When I tried to navigate public transportation for the first time and I felt so proud and brave, armed with directions scribbled on the back of an old receipt and exact change for bus fare. It was such a big departure from anything I was used to—jumping in my car and going, where I knew every back road and turn by heart. And then, on that first attempt, I ended up so lost, all turned around, and crying to Mike on the phone, because I had no idea how to tell him where I was, nor how to ask him to get me “home.” (Thank goodness that smart phones with GPS now exist.) But, I guess in that way you made me stronger. You made me tough. Resourceful. And, maybe most importantly, you taught me not to give up just because I got on the wrong bus, going in the wrong direction.

Now those days of getting lost and frustrated seem so far away. I know you better than I ever imagined. Actually, the thought of getting lost in a new city seems unsettling. I’m not sure if this new city will be worth it the way you were, Chicago.

Mike and I made our little home here, with you. Our first apartment together—it was such an exciting time. Learning how to live together and the importance of having two TVs (or His & Her TVs, as I like to call them). And so much happened in those 700 square feet. We became husband and wife there and began navigating married, grown-up life. The years from 25 to 30 are when we were forced to grow up, the real kind of growing up. Within those 4 walls, with no family nearby, is where we had to rely on each other, and you, and figure things out for ourselves, no matter how difficult or challenging it was. It’s where we battled homesickness, loss, doubt and worry. It’s also the home we gave our dog-child, Riggins, where we celebrated birthdays, anniversaries, holidays, professional successes, and small victories like finding street parking in front of our building, all five washers in the laundry room being available at once, or surviving another winter.

If I look back on the last five years with you, Chicago, many words come to mind: adventure, excitement, memorable. One that doesn’t? Easy. But, I guess “nothing worth having comes easy” though, right? Not that I necessarily expected our time together to be “easy,” I just don’t think I was prepared for how hard it might get. It’s strange sometimes living in a big city like you, constantly surrounded by energy, people and hustle, yet there were a lot of times I somehow felt really lonely—walking down streets, avoiding eye-contact, commuting on the bus, staring at my phone or a book, living in a building where I only knew faces, but not names. And then there were those times I felt all that shift, and we all felt so united and connected—festivals, concerts, St. Patrick’s Day, a parade, a Blackhawks’ win.

Please believe me when I say, I know a lot of the things I blamed you for weren’t really your fault. Like when the water heater burst that year and we were forced out of the apartment for 7 weeks, or when Mike’s car got broken into and they stole everything including a little bit of my faith in humankind. Or, those many times we had to drive around for over an hour in search of street parking, or how when we were deep into the winter months and I constantly wondered, “What the hell am I doing here? Why are we doing this to each other?” During those times, I know I took it out on you and that you felt the brunt of my frustrations and my anger. I’m sorry. Still, you didn’t let me walk away, somehow you knew when we were dangerously close to throwing in the towel and calling it quits, when I couldn’t stand it anymore, and you always picked me up and restored my hope.

The moment I realized that I loved you, was a little like déjà vu. Like maybe I had felt it before, years earlier, but hadn’t known what to call it yet, or had just been too reluctant to label it. It was fall, two years ago. I was walking the four miles home from work, I had just crossed over the La Salle Street bridge, the sun was setting and light reflected across the river, bouncing off every window pane of the surrounding buildings, the El passed by one bridge over, and because I couldn’t help myself, I stopped to take a picture, and thought, “I don’t want to be anywhere else right now.” In that moment, I let myself forget that there might be an expiration date on our time together. I believed it could be like this forever.

But, ironically, the best thing you ever gave me, Chicago, which I’ll always be grateful for, is time. Time with my best friends. Time when we weren’t quite ready to let go of college, but still excited for figuring out the future together. Time for us to make those real-life memories that sometimes seem even stronger than any other bond we had already forged.  To my sweet, best friends that helped make you feel like home, the ones that have been, and now will always be, my family, the ones you get to keep and that get to keep you, please take care of them.

Chicago, I’ll cherish it all—every memory, lesson, meal, summer, night out, night in, walk in the park, sunset, and someday I’m sure, even every snow. I know I’ll miss you. I’ll probably wish most of the time that things had happened differently. That we weren’t so far apart and that maybe I didn’t love you quite so much.

I often dream about the day, after Mike and I start a family, and we introduce you to our children. And we’ll probably take them to the Lincoln Park Zoo or to ride the ferris wheel at Navy Pier (although it will be a new and different one by then). The day we’ll get to say, “This is where mom and dad lived when we were young and fun, before we became parents.” When we were just two crazy kids with nothing to worry about but each other and the city.

I’m terrible at goodbyes. So, let’s agree to not say it. It’s not goodbye, Chicago. It’s see you later.

Love Always,


2 thoughts on “My Love Letter to Chicago

  1. This was so touching & brought tears to my eyes! Safe travels to you today and good luck on your new and exciting adventure! Wishing you and Mike all the best! Any time you are back in the Midwest, our home is always open to you! Will miss you!

  2. My heart is broken. Miss you two already. Cannot imagine life in this city without my best friend. Another beautifully written post by Hello Friday… Please keep documenting our/my life…. See you soon. #nonewrealfriends (is it appropriate to hashtag on a blog?!)

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