Chicago
Deep-dish pizza, world-class architecture, the blues, and windiest views
Chicago is America's second great city, and it refuses to be second in anything that matters. The architecture is spectacular: the city practically invented the skyscraper. The food scene goes far beyond deep-dish pizza. The blues and jazz heritage is living culture. The lakefront extends for miles of beaches, parks, and cycling paths. And the Chicago people have a directness and warmth that is entirely their own.
- 01Deep dish at Lou Malnati's
- 02Chicago-style hot dog at Superdawg Drive-In
- 03Italian beef sandwich at Al's Beef
- 04Sunday jazz brunch at Lonesome Rose
The architecture river cruise is the best $40 you will spend in Chicago
Free museum days vary by institution and day of the week, check ahead
The 606 elevated trail through Wicker Park is excellent in summer
Winter from December to February is genuinely very cold, dress in serious layers
Plan your Chicago trip
Get a personalised day-by-day itinerary built around your interests, dates and budget, in under a minute.
The most effective jet lag recovery approach, based on chronobiology
Light exposure, not melatonin, is the most powerful tool for resetting your circadian clock.
Most travellers are underinsured - here's the minimum you actually need
A single medical evacuation can cost $50,000-$200,000. Standard travel insurance often doesn't cover it.
our top pick in Chicago
things to do in Chicago
Hand-picked tours, activities and tickets, vetted by travellers
planning Chicago?
let AI do the heavy lifting.
Tell us how many days, who you’re traveling with, and what you care about. Get a complete day-by-day itinerary built from our curated experiences.