Photo: Jack Delano · Public domain · Wikimedia Commons
Photo: Jack Delano · Public domain · Wikimedia Commons
City Guide
The river, the lake, the neighborhoods, and a food debate that never ends. How to do Chicago in three days without just standing in line for deep dish.
Chicago is America's most honest big city. No one's pretending it's anything but what it is: a working town with world-class architecture, a chip on its shoulder the size of the lake, and opinions about pizza that can end friendships.
Three days gets you the river, the lakefront, two or three neighborhoods, and at least one argument about where the best slice is. (It's tavern-style, thin and cut in squares, and locals will fight you on this. The deep dish is for visitors, and that's fine, you're a visitor.)
The architecture boat tour is the rare tourist activity that locals will actually recommend. Ninety minutes on the Chicago River, and you'll understand why this city looks the way it does: the fire, the rebuild, the first skyscrapers, all of it narrated while you float past it.
Photo: Photograph: J. Crocker · Attribution · Wikimedia Commons
Afterward, walk the Riverwalk back toward the lake. Millennium Park is right there: Cloud Gate (the Bean), the Crown Fountain with its giant faces spitting water, the bandshell. It's free, it's fun, and yes, everyone takes the same photo. Take it anyway.
Downtown is for the postcard; the neighborhoods are for the trip. Wicker Park and Logan Square for the bars and the vintage shops, Pilsen for the murals and the Mexican kitchens, Hyde Park for the university and the lakefront that tourists never find.
Photo: flickr user mindfrieze · CC BY-SA 2.0 · Wikimedia Commons
And the music: Chicago invented entire genres here. A blues club on the South Side or a jazz set downtown isn't a tourist trap, it's the living culture. Go late, sit close, tip the band.
Beyond the pizza debate: the Italian beef (dipped, obviously), the hot dogs dragged through the garden (never ketchup, don't ask), the Polish and Puerto Rican and Vietnamese kitchens scattered across the neighborhoods. Chicago eats like the immigrant city it is.
Photo: Banpei at English Wikipedia · CC BY-SA 3.0 · Wikimedia Commons
Come hungry and pace yourself. Check what's on while you're in town too: the festival calendar here is ridiculous in summer, and the theatre and comedy scene runs all year. Second City started here, and the improv rooms are still the cheapest great night out in the city.
Get the Dayfari app — save events, get reminders, and plan road trips around them.