Chicago is a big, friendly, lakeside city with some of the finest architecture in the world. A glass-and-steel skyline rises beside a long public waterfront, and the neighbourhoods behind it have strong food, music and sporting traditions.
It is easy to get around and good value for a major American city, and summer brings festivals, beaches and outdoor dining.
How many days: 3
Three days covers the architecture, a museum or two, the lakefront and an evening of music. Two is enough for the highlights.
Use the elevated trains to link neighbourhoods, and keep an evening free for jazz or blues.
What to do in Chicago
- Take an architecture river cruise
- Boat tours along the river explain the history of the city's skyscrapers from the water. A popular and genuinely informative way to see downtown.
- Walk through Millennium Park
- A public park with a giant reflective bean sculpture, a fountain and a concert space. A good place to start in the city centre.
- Visit the Art Institute
- One of the great art museums of the United States, with a strong collection of impressionist and American art.
- Walk or cycle the lakefront
- A long path runs along Lake Michigan, with beaches, parks and views of the skyline.
- Go up a skyscraper
- Several towers have observation decks high above the lake. Go on a clear day, or at sunset.
- Spend an evening listening to live blues or jazz
- The city is a home of blues. Small clubs across several neighbourhoods have live music most nights.
- Explore a neighbourhood outside the centre
- Wicker Park, Pilsen and Hyde Park each have murals, shops and cafes with a local flavour.
- See a baseball game
- Wrigley Field is one of the oldest stadiums in the country, and a game there is a classic summer outing.
- Visit the Field Museum or the science museum
- Large museums with dinosaurs, ancient Egypt, and hands-on science. Good for a rainy day or with children.
- Stroll along the Riverwalk
- A path along the river links bars, cafes and public art, with views of the bridges.
- Visit Lincoln Park Zoo
- A city zoo beside a large park, with a lakeside walk nearby.
What to eat and drink
- Deep-dish pizza
- A thick, pie-style pizza baked in a pan, with layers of cheese and toppings. It takes time to cook, so order early.
- Chicago-style hot dog
- A hot dog with a long list of toppings, and famously no ketchup.
- Italian beef sandwich
- Thinly sliced roast beef in a roll, dipped in juices. A local classic.
- Tavern-style pizza
- A thin, crisp pizza cut in squares, popular with locals.
- Food from every culture
- Polish, Mexican, Greek and Ethiopian restaurants are found across the city.
- Craft beer
- Small breweries and taprooms are found in nearly every neighbourhood.
- Garrett-style popcorn
- A mix of caramel and cheese popcorn, a Chicago habit.
- Brunch
- Chicagoans love a long weekend brunch. Book ahead for the best places.
Getting around
The elevated trains and the subway form a network that covers downtown and most visitor areas. A contactless card or phone works on most.
Walking is pleasant in the centre, and the lakefront path is flat.
Ride-hailing apps are plentiful, and bikes are available for hire.
Good to know
- Winters are very cold and windy. Pack warm layers if you visit between late autumn and early spring.
- Summers are warm and busy, with many festivals. Book ahead for popular events.
- Tipping is expected in restaurants and bars.
- Prices on menus exclude tax, so allow for it.
- Visitors from many countries need an electronic travel authorisation. Check the official site.
- The wind off the lake can be sharp even in spring. A windproof layer is useful.
- Sports fans should check fixtures early, as popular games sell out.
- Neighbourhoods feel quite different. Pick two or three rather than trying to see them all.