Why Chicago’s Architecture is the Best in the World!!!

Since the election of former President Obama in 2008, folks who have never set foot on my block have had a whole lot to say about the city of my birth. Headlines dripping with doom. Comment sections full of experts who couldn’t find 79th Street with a GPS and a prayer.

So I decided to write about Chicago myself. Not as a tourist. Not as a pundit. Not as somebody flying in for a conference and leaving with a deep-dish pizza box and a stereotype.

I’m writing as a native. Born and raised. Except for seven cold, confusing months in Minneapolis when I briefly defected and then came running back home.

Because she was calling my soul.

Chicago. My home.

Let’s talk about the architecture.

He will always be Sears to me

Chicago is home to some of the most breathtaking architecture in the whole wide world. And I say that with my whole chest. This is the city that rebuilt itself after the Great Chicago Fire and basically said, “Fine. We’ll do it better.” That kind of audacity lives in the bones of the skyline. The Willis Tower (I still call it Sears), the poetic crown of the John Hancock Center, the majestic setting of the Field Museum — this city treats steel and glass like sculpture.

The Field Museum rising from the lake
The Cheesecake Factory is located here in the John Hancock building.

But I’m not just talking about the famous buildings framed in postcards and drone shots. I’m not just talking about downtown or the wealthier neighborhoods with their manicured lawns and security gates.

The Isidore Heller house designed by Frank Lloyd Wright
A castle down the street from the hood.

There are mansions on the South Side of Chicago that would make you stop mid-sentence. Solid brick. Limestone trim. Wide porches built for summer gossip and iced tea. Walk through places like Hyde Park, Kenwood, or the Jackson Park Highlands and you’ll see it — craftsmanship with backbone. Homes built when people expected structures to outlive them.

This mansion is in a predominantly Black neighborhood. Imagine that.

Chicago architecture isn’t just about height. It’s about history. It’s about a city that refused to stay down. A city engineered by immigrants, dreamers, hustlers, and stubborn Midwestern weather.

People love to reduce Chicago to crime statistics and political talking points. But concrete doesn’t lie. Brick doesn’t exaggerate. These buildings are evidence. They are proof of imagination, labor, and vision.

This city is layered — grit and grandeur, all at once.

And if you’ve lived here your whole life, you know: Chicago isn’t just something you read about. It’s something you walk through. It’s something that raises you.

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