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Things to do in Chicago

Skyscrapers on the river, city beaches on Lake Michigan and a theatre scene to rival Broadway. Chicago is the USA's most underrated big city.

Aerial view of Chicago and the beach on Lake Michigan

Chicago and Lake Michigan


Chicago's lakefront has around 26 miles of parks and beaches right next to the city centre.

The best things to do in Chicago

Chicago is known as the third coast because of its long shoreline on Lake Michigan. In summer, the city's beaches are full of swimmers, cyclists and volleyball players, just a few minutes from the skyscrapers of downtown.

Start with an architecture boat tour on the Chicago River, see the Cloud Gate sculpture in Millennium Park and visit the Art Institute of Chicago, one of the finest art museums in the USA. Read Picolo's guide to Chicago, the metropolis on the third coast.

The Chicago River and city centre

Riverside


The Riverwalk along the Chicago River is lined with restaurants, bars and boat tours.

Architecture and skyscrapers

Chicago is the birthplace of the modern skyscraper, and the city is a living museum of architecture. Look up at the Willis Tower and the John Hancock Center, both with observation decks, and see buildings by Frank Lloyd Wright, Mies van der Rohe and Jeanne Gang.

A river cruise is the best way to understand the city's history and design, from the Great Chicago Fire of 1871 to the glass towers of today.

Skyscrapers in Chicago

Skyscrapers


Chicago's skyline is one of the most famous in the world.

Theatre, music and food in Chicago

Chicago has around 250 theatres, from the grand venues of the Loop to small, experimental stages, and it is the home of improvised comedy. It is also a city of jazz and blues, with legendary clubs that have live music every night.

You cannot leave without trying a deep-dish pizza and a Chicago-style hot dog. The West Loop is the place for the city's best restaurants. For more destinations, see our USA holidays guide.

Theatre district in Chicago

250 theatres


Chicago's theatre scene is one of the most vibrant in the USA.

Best time to visit Chicago

Late spring to early autumn, from May to October, is the best time to visit Chicago. Summer brings beach days, festivals and outdoor concerts, while September and October are pleasant and less busy.

Winters are cold and windy, but the city is festive in December, and museums, theatres and restaurants make it a good city break all year round.

Chicago: frequently asked questions

How many days do you need in Chicago?

Three to four days is enough for a first visit to see the architecture, museums, the lakefront and a few neighbourhoods. With more time, add a day trip or combine Chicago with a road trip along Route 66 or a visit to St. Louis.

Why is Chicago called the Windy City?

The name is often linked to the strong winds that blow off Lake Michigan, but many historians believe it originally referred to the city's boastful politicians in the 19th century. Either way, winter winds can be very cold.

Can you swim in Lake Michigan in Chicago?

Yes. Chicago has many public beaches with lifeguards in summer, such as North Avenue Beach and Oak Street Beach. The water is cold early in the season but usually pleasant from July to early September.

What food is Chicago famous for?

Chicago is famous for deep-dish pizza, Chicago-style hot dogs with all the toppings, Italian beef sandwiches and a strong restaurant scene, especially in the West Loop.