Chicago travel guides & articles
All 5 in-depth pieces we’ve published on Chicago — newest first.
Chicago Is Where Modern Improv Was Born, and Still Lives
Second City taught the world how to improvise; six decades later, Chicago is still the city where you can watch it happen live, or learn to do it yourself.
The Pizza War Nobody Wins: Chicago's Deep-Dish vs Tavern-Style Divide
Deep-dish gets the postcards, tavern-style gets the weeknight loyalty — a route through both camps of Chicago's oldest food argument, no side-picking required.
Dragged Through the Garden: Chicago's Hot Dog Stands and the City's No-Ketchup Religion
A half-day-by-half-day guide to the Depression dogs, char-dog rivals, late-night stands, and the flagship that still tells the story of Chicago's most defended dish.
The City That Invented the Sky: Chicago's Architecture
A measured, half-day-by-half-day route through the city that built the first skyscraper — from the river that explains everything to Wright's suburbs and two houses that changed the world.
From Bronzeville to the Green Mill: Following Chicago's Living Jazz and Blues Lineage
A room-by-room guide to where Chicago's jazz and blues still play most nights of the week — what it costs, who each door suits, and when to turn up.