DO. SEE. EAT. DRINK.

DO. SEE. EAT. DRINK.

#008 CHICAGO: Layer By Layer

Wander past the familiar and you’ll find the layers that make Chicago unforgettable.

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DO. SEE. EAT. DRINK.
Sep 05, 2025
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DO. SEE. EAT. DRINK. is your weekly hit of what’s worth your time. Think of it as your cheat sheet to what’s inspiring, delicious, and can’t-miss. Then, on the first Friday of the month, we zoom out and drop a full city guide loaded with our favorite spots to stay, snack, and slow down.

Liquid sunset: The Garibaldi Banger at Bar Tre Dita.

If I just had a nickel for every time we’ve thought about moving to Chicago. It’s one of those cities that sneaks up on you. You think you know it as a visitor—architecture, the food, Lake Michigan—but then you start wandering and the layers start to show. Black history. Radical design. Deep, deep neighborhoods. Late-night tacos. Late-night perogies. Quiet parks tucked next to some of the greatest museums on earth. It’s got layers and contradictions, and just when you think you’ve figured it out, it hands you something new.

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