Chicago travel guides & articles
All 16 in-depth pieces we’ve published on Chicago — newest first.
Chicago in October for First-Time Visitors
What a first trip to Chicago should look like in the month of clear light, closed streets and free buildings, with the indoor fallbacks ready before you need them.
Chicago at Halloween Without a Single Haunted House
Halloween 2026 falls on a Saturday in Chicago, which packs a free Halsted parade, a 1921 movie palace, an aquarium after closing and Día de Muertos in Pilsen into one weekend.
Open House Chicago in Three Half-Days and Two Late Nights
Around 200 buildings open free of charge on 17 and 18 October 2026. Here is how to walk three of Chicago's districts properly instead of chasing the whole list.
Where Chicago Eats When It Isn't Eating Pizza
Two Michelin stars in a Filipino bakery, goat birria on Broadway, duck banquets in Uptown and a smokehouse on 95th Street: a full week of Chicago eating that never touches deep-dish.
A Chicago Weekend Around Doja Cat at the United Center
Doja Cat plays the United Center on Saturday 3 October 2026. The show runs two hours; what makes the airfare worth it is the weekend around it, where to eat, where to sleep and how to move.
A First Chicago Weekend Built Around the Lakefront
Two days of parks, museums, boats and observation decks strung along Lake Michigan, in the order that actually walks, with 2026 opening dates, prices and the bookings you cannot leave to chance.
Chicago's Speakeasy Circuit Behind Unmarked Doors
Sixteen Chicago rooms sit behind trapdoors, laundromats and takeout counters. Which of them poured through Prohibition, which take groups, and how to walk them in one night.
Planning a Chicago Marathon Weekend Without Wasting Your Legs
A four-day plan for the 11 October 2026 race: where to sleep for the shortest walk to the corrals, when to face the expo, what to eat, and how to see the city without spending a single mile on it.
Chicago's Basement Comedy Rooms After Midnight
A night-owl's route through the storefront theatres, dive-bar mics and after-hours club slots where Chicago's comics actually work, with prices, door rules and closing times.
Chicago's Decade of Rebuilding After the Great Fire
From a bronze pillar on a fire academy lawn to the glass prototype of the modern skyscraper, this is the ten-year rebuild that made Chicago the city it is.
How Chicago Turned Its Ashes Into a Steel Skyline
A walking itinerary through the landmarks, lobbies and hotels that prove Chicago rebuilt itself in fireproof stone and steel after October 1871, and never really stopped.
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.