A Love Letter to Chicago

A Love Letter to Chicago

It’s rare that I ever visit a place and immediately fall in love with it as hard as I did for Chicago. I remember when I first visited with my father during a summer vacation from high school. There was something about the Windy City that just…fit. Chicago isn’t the in-your-face-type New York City tends to be. It’s not nearly as glamorously superficial as Los Angeles. It doesn’t need to be; Chicago is its own kind of special.

I’ve found myself reminiscing quite often about my adopted second home. Is it because I left before I was totally ready? Or because my most recent trip back was a total whirlwind? It might be a combination of both. Regardless as to why I’m day dreaming so frequently about my college town (er, city? Lucky me) lately, I feel a need to profess my love in the only way I know how.


I decided to pay homage to my college town and adopted second home by penning this belated valentine to Chicago. As an expat abroad, I miss it dearly and am feeling lots of gratitude for the Windy City as it shaped me into the woman I am today. www.willfulandwildhearted.com

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Dear Chicago,

When I first arrived in 2007 as a bright-eyed freshman, I could’ve never imagined the impact you’d have on my life. You welcomed me – an awkward and troubled teenager – with open arms in the only way a Midwestern gal knows: with a tender heart and unmatched kindness.

Despite your warm personality, your frigid winters chilled me to the bone. I questioned my sanity for seven consecutive winters wondering how you managed to keep me around. Your hearty meals, cozy bars and thriving live music scene kept my body warm and my spirits high. 

And each summer, you pulled me back in.

a love letter to chicago

There’s something so exciting about a perfect Chicago summer day: a morning coffee on the porch, followed by an afternoon spent on the beach and the inevitable dance party or patio hangs in the evening. Your summers are special; frustratingly humid and, at times, chaotic, yet evoke a sense of stillness in my memory. Those six summers are still some of my favorite.

Chicago, it’s been three years since I left you behind, and nearly four years since I began to carve the path I’m on today. I’m so proud of the 19-year-old girl who was able to fearlessly navigate the city streets just as much as I am of the 25-year-old woman who ran away to Asia; much to the chagrin and confusion of many.

I get a pang in my stomach when I see photos of you; reminders of my past flood my thoughts and bring me joy, sadness and all emotions in between. I still have “fear of missing out” moments, wishing I could teleport into town for the day. But then I reflect on the past few years and realize I wouldn’t have all these experiences if it weren’t for my bravery and my openness to change – both of which came to fruition when I discovered you.

So, my dear Chicago, thank you for the precious memories, humbling me and for providing me with enough lessons to last a lifetime. Love you forever, boo. 

Where’s a place that will always be special to you?



  1. March 1, 2017 / 4:38 pm

    I completely agree that Chicago is its own kind of special. The first time I visited I really liked it but it wasnt until the second time that it became one of my favorite cities in the US. I do love NY, but there is something about it that makes me like it less and less every time I visit. Hope you get to visit again soon 🙂

    • March 1, 2017 / 6:23 pm

      I love NYC as well, but nothing compares to Chicago! There’s just something about it – glad you could see that side of the city as well!

  2. March 2, 2017 / 1:47 am

    Awe, I love this. I have been to Chicago a couple of times, but both times in the winter. I really like the area of Chicago that had the huge Japanese supermarket and restaurants. After reading this, it made me want to revisit but during the warmer months 🙂

  3. Megan Jerrard
    March 2, 2017 / 5:07 am

    This is a beautiful letter – I’ve heard many great things about Chicago, and also to avoid the city in winter!! But everyone raves about summer here, so I would love to travel to experience a little of the love affair it’s given you!

  4. March 2, 2017 / 12:02 pm

    I have a love/hate experience with Chicago, but I never lived there, only travel. Great photos, it looks like you have a wonderful time living there, and growing up. And yes, I recall too vividly those freezing winters and the chill to the bone cold.

  5. March 2, 2017 / 1:30 pm

    I loved Chicago the minute I got there, and I was only there for a long weekend. It’s a cool city. I know that that isn’t the same as the love from a person who has found their second home. My second home in Asheville, NC and I’ve been away from it for a while and I totally understand the pangs of missing out. Thanks for the beautiful, heartfelt letter. Xx

  6. March 2, 2017 / 5:16 pm

    I haven’t been to Chicago but your love letter makes me want to go! The good thing is that you can travel all around the world but Chicago will always be there to welcome you right back.

  7. March 2, 2017 / 8:06 pm

    I visited chicago in 2011 and I can tell you it’s an amazing place to visit. your pics describe your awesome experience there. Thanks for sharing.

  8. March 2, 2017 / 11:57 pm

    I am a native New Yorker, but I do like Chicago. I’ve only spent a week there but I am going back this summer. The architecture is really great and so is the food. In fact I like Chicago dogs better than NYC dogs. (Prefer our pizza though!) I’ve spent enough winters in Minneapolis with my grandparents that I’m not sure I’d want to visit the Windy City during winter though.

  9. March 3, 2017 / 3:35 am

    Such a beautiful letter. I see True love for Chicago in it. I totally understand the feeling of missing a place and remembering about all those memories that you created. All in all, the letter is just as amazing as the City itself.

  10. March 3, 2017 / 4:11 am

    I can’t believe I still haven’t been to Chicago! I’ve always wanted to visit, but never quite got over there (aside from a layover, which really never counts). I used to consider living there as well, though the windy reputation has made me more hesitant.

    This letter reminds me a bit of how I feel towards my college town. It was such a random place, but it was the first place I got to be on my own and start adulting, navigating my way through things, and figuring myself out a bit.

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