10 iconic things to do in Chicago

Bigger, faster, taller


The tallest

The Willis Tower (formerly the Sears Tower) is the tallest building in North America at 110 storeys. The John Hancock Observatory has super-speedy, 480-metres-per-minute elevators, and it’s also the place where you can stand and take in four states from one vantage point. Hello, Indiana, Illinois, Michigan and Wisconsin.

The first

The world’s first Ferris wheel made its debut in Chicago at the 1893 World’s Columbian Exposition. Visit Navy Pier and take a spin on a 15-storey replica of the original wooden wheel.

The coolest

Get your kicks by visiting the starting point of the historic Route 66—Buckingham Fountain in Grant Park.

The most highbrow

U.S. President Barack Obama and his wife, Michelle, are said to have included the Art Institute of Chicago on their first date. And why not—it has one of the world’s largest collections of Impressionist and Post-Impressionist paintings.

The funniest

It may be known as the Second City, but this is the first home of stand-up comedy and improv. Tina Fey, anyone? Make your way to the UP Comedy Club on a Monday night to see the Second City’s Improv All-Stars.

The deepest

Head to one of the many pizzerias offering the original Chicago deep dish in the city that invented it. You can even hop on a deep-dish pizza bus tour.

The windiest

Though it is technically not the windiest city in North America, the Chicago Tribune has suggested that Chicago’s windiest place is—arguably—the northeast corner of Jackson and Wabash.

The sportiest

Chicago is the birthplace of the 16-inch softball. Never heard of it? That’s OK; they also do regular baseball. Take in a Cubs game at world-famous Wrigley Field.

The most architectural

Famous buildings abound here. Feast your eyes on one of many architectural tours, from skyscrapers to the Inland Steel Building to the city-below-the-city Pedway system.

The bluesiest

Take in The Chicago Blues Festival, the largest, free blues festival in the world—three days, five stages and more than 500,000 fans—June 8 to 10. It’s the biggest of Chicago’s many music festivals and proves why the city can call itself the Blues Capital of the World.

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