How to Tackle Chicago as a First Timer
Planning a first-time visit to the Windy City? Home to extraordinary skyscrapers and pretty parks, world-class museums and top-notch bites, Chicago has something for everyone. To help you make the most of your first time in town, we’ve picked the city’s unmissable highlights—here’s what to add to your itinerary.
Ascend to the Top of the Willis Tower
Formerly known as the Sears Tower, the Willis Tower is one of the tallest buildings in the Western Hemisphere (for a time, it was No. 1 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.
Explore Millennium Park’s Art and Gardens
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 landmarkCloud Gate (better known as “The Bean”). Explore on foot, or speed along on a bike or Segway tour.
Try Authentic, Chicago-Style Pizza
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.
See the City—and Its Architecture—by Boat
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.
Visit the Masterpieces at the Art Institute of Chicago
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.
Discover the Windy City’s Prohibition History
Chicago was once frequented by infamous gangsters 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.