Blown Away by the Windy City

Chicago has this bold, cinematic presence with towering architecture, a river that slices through downtown like a runway, and neighborhoods that feel like their own little worlds. What surprised me most was not the skyline or the deep dish, although both are unforgettable. It was how many quirky and delightful facts the city hides in plain sight.

Here are some of my favorites from our visit:

🧅 A city named after a wild onion

New York may be the Big Apple, but Chicago’s name comes from the Algonquian word shikaakwa, meaning wild onion or skunk cabbage. Early explorers noted the strong smell of these plants along the riverbanks and the name stayed. It gives the city an unexpectedly earthy origin story.

🚂 The Loop and its elevated soundtrack

Downtown Chicago is called The Loop, a name that comes from the elevated L train tracks that loop around the central business district. You can hear the trains rumble overhead as you walk, creating an urban soundtrack that feels straight out of a movie.

🏢 A building with its own ZIP code

The Merchandise Mart is four million square feet of pure architectural confidence. For decades it was the largest building in the world and it even had its own ZIP code until 2008. Standing in front of it feels like standing at the base of a man made canyon.

🍀 A river that turns bright green

Chicago takes St. Patrick’s Day seriously. Every year the city dyes the Chicago River a vivid green using an eco friendly vegetable based dye. Watching an entire river glow is surreal in the best way.

☁️ Buildings shaped by the river

Many of Chicago’s riverfront buildings were intentionally designed to reflect the water or curve with it. One of the most iconic is 333 Wacker Drive, the shimmering green glass building where Ferris Bueller’s dad worked in the movie. It mirrors the river so perfectly it almost blends into it.

🌊 A river that flows in reverse

In one of the most ambitious engineering projects of the early 1900s, Chicago reversed the flow of its river. Instead of draining into Lake Michigan, it now flows toward the Mississippi River. The project reshaped the city’s future and protected its water supply.

🍕 Deep dish dreams at Lou Malnati’s

You cannot talk about Chicago without talking about deep dish. Lou Malnati’s is a must for anyone who wants to experience the city’s world famous pizza. It is cheesy, saucy, buttery perfection that feels like a warm hug in a pan.