So, I just got back from Chicago, and wow—I'm still buzzing from the whirlwind that was my trip. I mean, when I think of the best things to do in Chicago, I always thought I'd be looking up skyline selfies and stuffing my face with deep-dish pizza. But honestly, it turned into so much more than that. Let me tell you about it over this cup of coffee I probably should have finished ten minutes ago.
This spot? Total surprise.
I didn't mean to end up at that little café in Pilsen called Cafe Jumping Bean—I was actually just wandering around after getting off the Pink Line. I had marked a few spots on Google Maps, but somehow, my sense of direction led me to this charming hole-in-the-wall instead.
At first glance, I wasn't sure. The decor was all mismatched tables and colorful walls that felt like they were washed in warm light, and the scent of freshly brewed coffee just wrapped around me like a hug. I wasn't expecting much; I figured it would be a quick caffeine fix before heading to my “actual” destination. But then I saw the barista whip up this colorful matcha latte, and suddenly, I was glued to the counter watching her like I was at a magic show.
The strangest thing? She noticed I was fascinated and started chatting with me about where espresso beans come from. I hadn't planned on deep coffee discussions, but we ended up talking about everything from the local art scene to the best taco trucks in the area. It felt like the kind of spontaneous detours you read about but never actually experience. And that matcha latte? I still can't stop thinking about it. It was vibrant, creamy, with a hint of sweetness that just hit the spot.
The afternoon that changed my whole mood
You know how sometimes you're just kind of wandering, feeling a bit listless? Well, that afternoon really shifted everything for me. After my spontaneous coffee detour, I decided to walk over to the Art Institute of Chicago. I told myself, “It's just one more museum, right?” But I wasn't prepared for the emotional rollercoaster of seeing A Sunday on La Grande Jatte up close. That painting is massive—like bigger than I imagined.
As I stood there, taking in all those tiny brush strokes, I was hit with this odd wave of nostalgia—like, I felt like I was standing in my college art history class, discussing the piece with friends who were also trying to appear knowledgeable but really just wanted to know when we could leave for drinks. I don't know why I felt so strongly; maybe it was the combination of art and the way sunlight streamed through the windows of the museum.
But as I took a step back, another visitor bumped into me. I turned, ready to tell them to watch it, but instead, it was this older gentleman who looked as moved as I felt. We ended up chatting about the piece, discussing our interpretations—like we were part of some odd, temporary art club. He told me about his granddaughter who just graduated with an art degree, and honestly, I could've listened to him for hours. It was the kind of human moment that makes travel feel worthwhile, you know? Just connecting with a stranger over something beautiful.
I almost missed this, no thanks to my bad sense of direction
Here's the thing: I'm terrible with directions. It's a miracle I found my way around the city at all. After hanging out at the Art Institute, I thought I'd stroll over to the Millennium Park to check out the Cloud Gate—or as most people know it, “The Bean.” I swear, I had Googled it multiple times, but between my wandering mind and a detour to find a public restroom, I ended up on the opposite end of the park.
After some aimless walking (and maybe a little muttering about Chicago's grid system), I finally stumbled across it. And wow. You know that moment when you see something in person that's just been a part of your life through photos? It felt surreal standing there, seeing the reflective curve towering over me, flipping the skyline back at me. Instead of just snapping a photo and moving on, I found a bench nearby and just… sat there, reflecting. It's funny how sometimes getting lost pulls you to exactly where you need to be.
And then I met a family—they were just as enchanted and started taking goofy family pictures. I got suckered into being the unofficial photographer for them. Nothing major, just snapping some silly shots, but it felt intimate. We were all strangers in this big city, united by a shiny bean.
A meal I still can’t shake
And then? Oh, the food. So, I made my way over to the West Loop, drawn by the collective raving of famous restaurants. I hadn't made any reservations (rookie mistake), and the line outside Girl & the Goat was ridiculous. I almost gave up, thinking maybe I'd settle for something boring. But when I lingered outside, I overheard someone inside talking about roasted pig face, and I was instantly intrigued.
I was about to leave when I noticed a bar area. No reservations needed! There's something about being able to walk up to a bar, grab a seat, and talk to the bartender about what to eat that felt so much more inviting. I ended up ordering a few small plates, including that infamous pig face, which, if I'm being honest, sounded gross but was unbelievably good. Crispy skin, oh my god.
The flavors danced on my tongue, and I was mid-bite when I struck up a conversation with the couple beside me. They had been coming here for years and shared their favorite dishes. It turned into this lively chat about Chicago food and hidden gems I'd have to check out. We laughed like old friends, bonding over food and our shared experience. I left with a full stomach and a couple of new recommendations, which felt pretty darn good.
So, yeah, that was Chicago for me. A city that surprised me at every corner, with moments weaving together into something unforgettable. The best things to do in Chicago were less about the places I'd pinned on my map and more about the unexpected encounters and delicious bites I stumbled upon.
And here I am, still sipping this cold coffee and soaking it all in, wishing I could relive those moments just one more time.
