Visiting Chicago for the First Time? Here's What to See and Do

Formerly known as the Sears Tower, the Willis Tower is one of the tallest buildings in the Western Hemisphere (for a time, it was the tallest in the world). There are few more classic Chicago experiences than taking a lightning-fast elevator up to its Skydeck, where you can admire extraordinary city panoramas. Book early morning VIP tickets to see it sans crowds—and step onto the glassed-in ledge if you dare.

Chicagoans take their pizza seriously—and whether you’ve got a hankering for the classic deep-dish offerings or want to try the city’s thin-crust alternatives, pizza-centric walking tours offer the perfect culinary survey.

Among the city’s top museums, the Art Institute of Chicago boasts a sprawling collection, which encompasses some 300,000 objects. Make like Ferris Bueller and get up close and personal with its masterpieces—artworks by Georgia O’Keeffe, Pablo Picasso, Marc Chagall, Georges Seurat, and Edward Hopper number among its highlights.

One of the niftiest ways to explore downtown Chicago—and see many of its top landmarks in just an hour or two? Hop aboard a boat tour. As you wend your way along the Chicago River, spy Windy City architectural icons, and learn how they were built. Alternatively, trawl the waters of Lake Michigan to discover Chicago’s own inland sea.

Chicago was once frequented by infamous gangsters, including the likes of Al Capone, and the advent of Prohibition in the 1920s saw its number of speakeasies—and sordid happenings—soar. Embark on a one-of-a-kind history tour to learn about this memorable moment in Chicago’s past, and even drop by the city’s trendy, modern-day speakeasies to indulge your inner flapper.

An oasis of green amidst the Loop’s soaring skyscrapers, busy shopping streets, and rumbling L trains, Millennium Park offers a wealth of cultural and aesthetic highlights. A top Windy City attraction since 2004, the park comprises gardens, event spaces, and public artworks—including Anish Kapoor’s landmark Cloud Gate (better known as "The Bean”). Explore on foot, or speed along on a bike or Segway tour.