Itineraries for Your Trip to Chicago
2 Days in Chicago for First Timers
I might be biased—I was born and raised in the Windy City—but if you ask me, Chicago isn’t just one of the most thrilling cities in the US: It’s one of the best cities I’ve ever been to. Though often overlooked in favor of coastal hubs like New York and Los Angeles, Chicago more than holds its own. Its skyscrapers are some of the world’s tallest, its museums among the country’s best—and then there’s its world-class dining scene.
It’s no wonder that I return to the Windy City every chance I get, and regularly advise first timers to make the trip. If you’ve got two days in Chicago planned, make the most of all the city has to offer with this introductory itinerary.
If you only have time for one thing, make it exploring the skyscrapers, parks, and public artworks of the downtown Loop.
Despite its nickname, Chicago isn’t as windy as you might expect—however, it does get icy cold in winter and steamy hot in summer, so pack seasonally.
Beloved by locals and out-of-towners alike, cruising along the Chicago River isn’t just a relaxing experience on the water—it’s also a time-saving way to discover many of the city’s best-known skyscrapers and landmarks. Crane your head as you glide right past attractions from the John Hancock Center to Marina City and Navy Pier, and learn the stories behind the sights from your guide’s narration.
Chicago’s food scene is almost as famous as its architectural icons, and for good reason—whether your tastes run to hearty favorites like deep-dish pizza and Italian beef sandwiches or Michelin-starred fine dining, the city’s got it all. If you’re feeling hungry after your river cruise, then all the better: Lunch is the perfect time to book a tasting tour and try a range of Chicago favorites.
As the sun starts to set, it’s time for a different—and decidedly more insalubrious—kind of tour. The Windy City has its dark side, and on an evening gangsters and ghosts tour, you’ll discover the days when the Loop was home to speakeasies and notorious characters like Al Capone. Spot landmarks you’d otherwise walk right by—and even hear tales of supposedly hauntings as you go.
If your first day provided an overview of Chicago’s highlights and history, then day two is the perfect opportunity to get a closer look. Start your morning with a walking tour that takes you right inside the city’s architectural highlights. Discover the Chicago Cultural Center’s Tiffany glass dome, visit art deco masterpieces like the Chicago Board Of Trade Building, and explore other highlights that are hidden at street level.
After grabbing a quick lunch, continue your Chicago cultural immersion by heading to one of the city’s celebrated museums. The Field Museum of Natural History is a great choice for visitors of all ages: With prebooked entry, you have the flexibility to explore its dinosaur skeletons, rare gemstones, taxidermy critters, and other exhibitions at your own pace.
For a showstopping city like Chicago, it’s worth ending your trip in style. The Willis Tower (formerly known as the Sears Tower) was once the world’s tallest building, and its Skydeck Chicago observation deck is still one of the city’s most astounding sights. Time your visit with sunset to see the lights coming on all across Chicago for a particularly magical conclusion to your getaway.
