So, I just got back from Chicago, and wow, let me tell you, the best things to do in Chicago are not what I expected. Seriously, that city is like a treasure chest of surprises. You think you know a place from brochures and Instagram pictures, but when you're actually there? Everything is different. I mean, honestly, in my head, I thought I was in for a typical tourist experience—jumbled tour buses, overpriced hot dogs, and long lines at every museum—but boy, was I wrong.
This spot? Total surprise.
First up, I stumbled upon this little café called Intelligentsia. Now, I know Chicago has a vibrant coffee scene, but I had no idea how deep the rabbit hole went until I walked in. It wasn't one of those over-the-top Instagram-worthy places with pink walls and botanical vibes. No, it was more like a caffeine sanctuary, filled with serious baristas who looked like they could turn a bag of beans into something magical. I swear, the beans were talking to me, saying, "Drink us!"
I tried their pour-over and, honestly, I think I might have overreacted a little. The flavors burst in my mouth and made me feel like I was tasting coffee for the first time. I just nodded dumbly, grinning like a child at a candy store. A few patrons glanced at me, probably thinking, “This girl needs to chill,” but can you blame me? I wasn't expecting such an explosion of flavor. I sat there for over an hour just absorbing the atmosphere, half-amazed at my happy little accident.
The afternoon that changed my whole mood
You want something that really turned my outlook around? That would be a spontaneous visit to the Art Institute of Chicago. I hadn't planned on going there—museums can be a little dull for me—but I ended up wandering in after a hotdog food truck caught my eye. Yeah, you can take the girl out of New York, but I still can't resist a good street dog.
Anyway, I figured, “What's next anyway? Just some boring art?” But the moment I stepped inside, I was like a kid in a candy store again. The way they displayed everything—the colors, the architecture, the sheer scale of it all—was breathtaking. I found myself staring at a Monet, entranced by those hazy colors, around a group of people who were all just as captivated. I didn't even care that I hadn't prepped myself for this. I found solace in that little moment of shared awe.
And you know what? I left that place feeling lighter, as if the chaos of the world had just vanished for a few hours. I can't explain it, but the quiet beauty of art just wrapped itself around me like a warm blanket.
I almost missed this, no thanks to my bad sense of direction
One part of the trip that was a complete whirlwind was my attempt to navigate the L train. You'd think that with Google Maps, I'd be fine, right? Well, let's just say my sense of direction is comparable to a raccoon with a GPS. I found myself wandering down Wabash instead of State Street, and out of frustration, I stopped at this small park. I don't know why I ended up there, but it turned into a small oasis of weirdness.
There was this group of older folks playing chess, seriously battling it out like it was life or death. I pulled up a bench and just watched for a bit. They were so into it that I felt like I was transported to some other time—a time when life wasn't thrown at you through screens every minute. At that moment, I realized how beautiful those little spontaneous experiences can be.
Suddenly one of the players, noticing me, started sharing his strategies, all while muttering about how no one plays chess anymore. I laughed and pretended to care, but in reality, I was just hanging onto his words like lifebuoys in a sea of confusion.
A meal that lingers in my thoughts
And oh boy, let's talk about food because honestly, I could write a whole book about that pizza alone. So, I went to this place called Pequod's. Now, I love a good deep-dish, but you know how everyone raves about it? I mean, I thought it might be overhyped. But then—my first bite—oh my God, it was like the heavens opened up, and the angels were singing.
The crust was so perfectly caramelized, it was like they took a whole new approach to pizza science. And the layers of cheese! I felt my heart flutter, and I knew I'd have to share it later but I mean it would have been a crime not to take that first slice all by myself. My waitress was this bubbly person who probably realized how lost I looked when I couldn't decide what to order. I told her it was my first time in Chicago, and she just grinned, “Well then—deep dish it is!”
By the end of that meal, I was in a happy food coma. I don't even know how I managed to waddle back to my hotel afterward. But those simple, even clumsy pleasures are what made Chicago stick in my heart.
When I wrapped up my last night, sitting on my hotel room bed with leftover pizza and a half-finished novel, I realized that the best things to do in Chicago are not just great spots to check off a list; they're about connecting—whether it's with a piece of art, a stranger at chess, or the flavor of a deep-dish pizza that ignites something more profound inside you.
As I finish this last sip of coffee, I can't help but feel the echoes of Chicago tugging at me, a bit messy and chaotic, just like the experience itself. Life in that city felt so raw, so real. I'm already daydreaming about going back.
