Chicago
Chicago delivers world-class architecture, deep-dish pizza, and lakefront beauty at a fraction of the cost of New York or San Francisco. With a robust transit system, free museum days, and some of the best cheap eats in America, the Windy City punches well above its weight for value travelers.
Why go to Chicago
Millennium Park & Cloud Gate
Iconic free public art and skyline views that rival any paid attraction in the world.
Art Institute of Chicago
One of the greatest art museums on the planet, housing Seurat, Hopper, and Picasso under one roof.
Chicago Architecture Boat Tour
A narrated river cruise past 50+ landmark skyscrapers that will leave you genuinely awestruck.
Navy Pier
Festive lakefront hub with a Ferris wheel, free fireworks, and sweeping Lake Michigan panoramas.
360 Chicago or Willis Tower Skydeck
Step onto a glass ledge 1,353 feet up and look straight down at the city grid below.
Make it real
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Good to know in Chicago
- The CTA Ventra card covers both the El train and buses for $2.50/ride or $5/day unlimited, buy at any station kiosk and skip taxis entirely.
- Tipping 18-20% is firmly expected at sit-down restaurants; 15% is acceptable at counter-service spots but skipping it is noticed.
- Chicago tap water comes from Lake Michigan and is consistently rated among the best-tasting municipal water in the country, carry a refillable bottle.
- The Art Institute of Chicago offers free admission Illinois residents on select Thursdays, and teens 14-17 are always free; check choosechicago.com for free museum days across the city.