If you won two free plane tickets, where would you go?
Chicago. No hesitation.
It’s not just because of the iconic skyline or the pizza, though let’s be honest—those things do help. I’d take my mom. We had actually discussed this during my recent trip to see her this summer. There’s a Frank Lloyd Wright house she’s always wanted to see, and as fate (or clever set design) would have it, I spotted that same house in an episode of The Bear the other night. I didn’t know she was such a fan of his architecture until recently, but now that I do, I’m impressed. Yes, I’d like to see it too.
And while we’re at it, I’ve got my painter’s eye on The Bean. Yes, I know it’s officially called Cloud Gate, but let’s be real—we all call it The Bean. There’s something almost magnetic about it, especially given the long-standing feud between Anish Kapoor and Stuart Semple. (Artists and their dramas. We love to see it.)
Plus: museums, neighborhoods with character, parks, public art, the lake, the layers. Chicago seems like the kind of place that tells you a thousand stories in the space of a single block.
So if I had two tickets? No contest.
Chicago. My mom and I. A couple of days of architecture, art, and adventures.
Hold the deep dish—I’m more of a thin crust girl.


