You know, I just got back from Chicago, and honestly, I'm still buzzing from the whole experience. If you're craving a little adventure, I have to say, I've uncovered some of the best things to do in Chicago that just caught me off-guard. The whole trip was like a delightful jumble of surprises, good eats, and those little messy moments that just made everything feel… real. You know?
This spot? Total surprise.
So picture this: it's my first afternoon in the Windy City, and I'm wandering around, trying to find my bearings. I'm aiming for the famous Millennium Park; it sounds cliché, but I'd read about the Bean, and I figured I had to see it. Somewhere along the way, I started to doubt myself. I mean, what if the park was just a tourist trap? But then, I stumbled into this small tucked-away joint called Lou Malnati's. I wasn't planning on pizza right away, but man, the smell wafting from that place was heavenly.
I thought, “Why not?” I walked in and ordered a classic deep-dish pizza, totally embracing the chaos of my food choices. Sitting there, waiting for it, I was struck by the buzz around me: families chatting, a couple on a date, solo travelers like me, all digging into these gigantic slices. When my pizza finally arrived, it was nothing short of an art piece—a masterpiece of gooey cheese, rich tomato sauce, and a buttery crust.
Each bite was overwhelming in the best way possible, and just like that, I had gone from feeling skeptical about the city to completely hooked. Honestly, I wasn't expecting much from a pizza place, but it turned out to be a pivotal moment in my trip.
The afternoon that changed my whole mood
Later that day, I hopped on a city bike—yes, because I believed the “city bikes are super easy” motto. Spoiler alert: I found out my sense of direction is basically non-existent. I ended up biking along the lakefront, the breeze cooling my face. At first, I was confused, thinking, "Where am I going?” but then—to my pleasant surprise—I found myself at North Avenue Beach.
Somehow, I wasn't alone out there. It was gorgeous! People were sunbathing, kids were splashing about, and everyone just seemed to be thriving. I didn't pack a swimsuit or anything, but I set my bike down, dipped my feet in the water, and let the waves gently lap against my ankles. That moment — just standing there, toes in the cool water, looking out at the skyline — felt incredibly freeing. I thought, “This is what life is about.” It was as if all the worries I had before the trip just melted away in that lake breeze.
I ended up talking to a group of locals who invited me to join their impromptu game of beach volleyball. Now, I don't play volleyball, but you bet I jumped in anyway. We laughed, fumbled the ball around, and I left feeling like I'd made a connection, even if it was a fleeting one. It's those small moments that stick with you, right?
I almost missed this, no thanks to my bad sense of direction
My last day in Chicago was chaotic in the best way. I had been planning to visit the Art Institute, a must-see for sure, but I got sidetracked. I can't quite remember how it happened, but I got lost—and, honestly, I don't know why I ended up in the Pilsen neighborhood. This area is known for its vibrant murals and artwork, and as soon as I turned the corner onto 18th Street, I was taken aback. I had stumbled into an impromptu street art gallery!
These murals were gigantic and bursting with color. There was such a rich sense of community here, both in the murals and the little shops lining the streets. It wasn't on my itinerary, but it felt like fate, like the city wanted to show me something special. I found this little café called Café Jumping Bean, and trust me, the coffee was out of this world.
I sat outside with my latte and a pastry, just poking around the shops while listening to a street musician—it completely shifted my mindset. I hadn't expected to feel so at home in a city I was just visiting. I got lost, but in that lostness, I found something way cooler.
After wandering around for a while, I finally made my way back to the Art Institute. I think the universe said, "Chill, you don't need to rush." And can we talk about the Impressionist collection? I could've just stared at Monet's “Water Lilies” forever, feeling completely enveloped by the beauty. Art does that, I suppose; it pulls you in and transports you into another world.
The moment that will stick with me
As I sat on the steps of the museum, watching a sunset that just exploded into vibrant oranges and purples over the city's skyline, I felt grateful. I reflected on the entire trip—those unplanned moments, the surprise connections, and all the funky little mess-ups along the way. Every wrong turn had led me to something delightfully unexpected.
I headed to the airport, tired but blissfully content, feeling a bit different in the best way. I think that's what traveling is about: letting go of our plans, diving into the messiness, and just being open to whatever happens. The best things to do in Chicago are not just the big attractions but those little moments—unexpected friendships, spontaneous adventures, and the overwhelming beauty of the city itself.
As I sip the last dregs of my coffee right now, I can still feel the echoes of Chicago in my heart, a place that turned out to be full of surprises. And honestly? I can't wait to go back.
