Chicago is the USA's architectural showcase — the birthplace of the skyscraper, strung along a vast freshwater lake with beaches, a lively food scene and deep blues and jazz roots. Big-city energy with Midwestern warmth, and the start of Route 66.
- World-class architecture — take the river boat tour to see it
- Lakefront beaches, parks and the Millennium Park 'Bean'
- Blues, jazz and comedy heritage (Second City, Chess Records)
- Deep-dish pizza, Italian beef and a serious dining scene
Region: Midwest Best time: May–Oct (warm, lakefront in bloom); winters are cold and windy but festive Getting there: O'Hare (ORD) is a major global hub; Midway (MDW) is closer for domestic flights. Both connect downtown by 'L' train. Getting around: The 'L' elevated trains and buses plus walking cover the core; the lakefront has a long bike and running path.
Neighbourhoods
The Loop
The downtown core — skyscrapers, the Art Institute, Millennium Park and the theatre district.
River North & Near North
Galleries, dining and the Magnificent Mile shopping strip.
Wicker Park & Bucktown
Hip, indie shops, music venues and some of the city's best restaurants.
Pilsen
Vibrant Mexican American neighbourhood with murals and the National Museum of Mexican Art.
Hyde Park
South-side home of the University of Chicago and the Museum of Science and Industry.
Things to do
- Architecture river cruise — the single best introduction to the city, from the water
- Millennium Park — Cloud Gate ('the Bean'), the Pritzker Pavilion and Crown Fountain
- The Art Institute — a top-five US art museum right on Michigan Avenue
- Skydeck or 360 Chicago — glass-ledge views from Willis Tower or the Hancock
- Lakefront day — bike or walk the path to North Avenue Beach and Lincoln Park Zoo
- Blues & comedy — a South-side blues club or a Second City improv show
A few perfect days
- Day 1Downtown icons
Architecture river cruise, Millennium Park and the Art Institute, dinner in the Loop.
- Day 2Neighbourhoods
Wicker Park and Pilsen by day; a blues club or comedy show by night.
- Day 3Lake & sky
Skydeck views, then the lakefront path and a beach afternoon; deep-dish for dinner.
Eat & drink
- Deep-dish pizza and thin-crust tavern-style, plus a Chicago-style hot dog
- Italian beef sandwich, dipped, with giardiniera
- Diverse eats in Pilsen (Mexican) and Chinatown; craft beer citywide
Tickets & tours
Skip-the-line tickets and tours in Chicago, booked through our partners.
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Chicago: Art Institute Ticket & Audio Tour Book → -
Chicago: Field Museum of Natural History Ticket Book → -
Chicago: Field Museum Ticket & Audio Tour Book → -
Museum Of Contemporary Art (MCA): Entry Ticket Book → -
Chicago: Museum of Science and Industry Ticket & Audio Tour Book → -
Skydeck Chicago Book on Tiqets →
National parks & day trips
Where to stay
Compare hotels and rentals across Chicago.
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