City guide
Chicago
Chicago pairs big-shoulders architecture with a genuinely walkable downtown: deep-dish pizza, an elevated 'L' train rattling past skyscrapers, and a Lake Michigan shoreline that turns the Loop into a beach town every summer. It is a serious food and museum city with none of the coastal glamour of LA or New York, which is part of the appeal, but the winters are long, dark and cut through by lake wind.
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Chicago travel guides
Planning around events? These guides collect 2026 calendars, festival clusters, and practical trip ideas so you can compare dates before you book.
Top things to do in Chicago
The most popular sights, with 2026 entrance fees. Prices are adult admission — cheapest at the gate. Many of the best things are free.
| Attraction | Entrance | Time | Why go |
|---|---|---|---|
| Cloud Gate (Millennium Park) | Free | 30-45 minutes | A reflective stainless-steel sculpture by Anish Kapoor, nicknamed 'The Bean,' set on the free public grounds of Millennium Park in the Loop. Its polished surface mirrors the surrounding skyline and draws visitors for photographs throughout the day and evening. |
| Art Institute of Chicago | Varies | 2-4 hours | An encyclopedic art museum on Michigan Avenue holding collections spanning ancient to contemporary art, including Grant Wood's American Gothic and Seurat's A Sunday on La Grande Jatte. It is one of the largest art museums in the United States by gallery space. |
| Navy Pier | Free | 2-3 hours | A 3,300-foot pier on Lake Michigan combining gardens, a Ferris wheel, restaurants, and performance venues, including the Chicago Shakespeare Theater. General admission to the pier grounds is free; individual rides and attractions are ticketed separately. |
| Skydeck Chicago | $32 | 45-60 minutes | The 103rd-floor observation deck of Willis Tower, formerly the world's tallest building, featuring glass 'Ledge' balconies that extend outward from the tower face. Views on clear days extend across four states. |
| Shedd Aquarium | Varies | 2-3 hours | A lakefront aquarium housing more than 32,000 animals across marine and freshwater exhibits, including a Caribbean coral reef and beluga whales. It opened in 1930 and remains one of the largest indoor aquariums in the country. |
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Plan your stay in Chicago
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Getting to Chicago
Accommodation options for Chicago are listed above, alongside travel essentials for your trip.
2026 guides
Planning around events? These guides collect 2026 calendars, festival clusters, and practical trip ideas so you can compare dates before you book.