Bursting with history and culture, Chicago is one of the United States’ most vibrant cities. So it should come as no surprise that over 50 million people flock to the Windy City each year to soak in all that it has to offer. Filled with greenery, incredible architecture, and world-class museums, there’s no shortage of things to see and do when making a visit to Chicago.
Art and culture lovers will particularly appreciate the possibility to learn about American architecture, enjoy a world-class art collection, and stroll by cutting-edge contemporary public art. These opportunities speak to Chicago’s enduring reputation as a place of culture, whether that means holding the World’s Fair in 1893 or commissioning Anish Kapoor’s Cloud Gate for Millennium Park.
So what should be at the top of your list the next time you visit Chicago? After you’ve figured out where to stay and what to eat using our Chicago travel guide, there are a number of must-see sites and activities. You can start planning your trip with more info on some of our favorite spots below, to make sure you don’t miss any of the art, architecture, and history that the city has to offer.
Looking for things to do in Chicago? Check out these places.
Chicago Architecture Center River Cruise
If there’s one thing to do while in Chicago, it’s most certainly the Chicago Architecture Center’s river cruise. As you float down the Chicago River, a knowledgable Chicago Architecture Center docent will narrate the history of the city. Using Chicago’s iconic architecture, the guide takes participants on a journey through the development of the city and how it moved from a small settlement to the metropolis we see today. Taking only 90 minutes, it’s a quick, easy way to get a basic overview of the city and you can visit the new Chicago Architecture Center afterwards to get even more in-depth info about Chicago and its architecture.
Tip: If you’re an architecture lover, try the Chicago Architecture Center’s excursion outside of Chicago to the Mies van der Rohe-designed Farnsworth House.
Art Institute of Chicago
As one of the United States’ oldest and largest museums, the Art Institute of Chicago has a collection that cannot be missed by any art lover. Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday on La Grande Jatte, and Grant Woods’ iconic American Gothic are just some of the incredible highlights of the museum. The building itself is also rich in history, having been constructed for the World’s Fair. A recent expansion by renowned Italian architect Renzo Piano not only added a contemporary edge to the site, but has allowed the museum to greatly expand what is on display.
Tip: Use your time wisely and take advantage of mobile tickets to the Art Institue of Chicago that will let you breeze through the doors and start your exploration of the museum without waiting.
Since opening in 2004, Millennium Park has become a Chicago icon. Located within Grant Park—which is home to the historic Buckingham Fountain—it’s a top tourist destination. Of course, one cannot visit Millennium Park without taking in Anish Kapoor’s Cloud Gate and Frank Gehry‘s Pritzker Pavilion which have become mascots for the city.
Tip: Taking an evening bike tour around Chicago which allows you to be active and cover enough ground to see Millennium Park and much more.
Perhaps nothing speaks to Chicago’s 19th-century economic boom more than its theaters. The proliferation of theaters built at the end of the 19th century speaks to the population’s push to make Chicago a cultural hub on the level of New York, Paris, and London. Today, there are over 250 theaters in the city, but perhaps one of the most iconic is Auditorium Theater. After opening in 1889, it has played host to incredible talents like Sarah Bernhardt, The Ziegfeld Follies, Janis Joplin, and Jimi Hendrix. It’s also staged numerous Broadway musical and ballet performances by prestigious companies. Innovative right from the start, the building had design features that were unheard of at the time like air conditioning and hydraulic lifts to raise and lower the stage.
Tip: Explore this National Historic Landmark in a tour that examines the magnificent design and history of the theater.
A visit to Chicago’s suburb of Oak Park means a lesson in the architecture of Frank Lloyd Wright. Perhaps no other architect was as influential in shaping American design and Chicago, where he got his start. Oak Park is not only the location of Wright’s iconic Prairie School residences, it’s also where he had his home and studio. The newly restored Unity Temple is also an incredible opportunity to see the interior of a public building done in the Prairie style.
Tip: Spend a half-day tour unraveling the history of Frank Lloyd Wright’s early architecture.
To truly take advantage of all Chicago has to offer, don’t forget to book your CityPASS. This allows you to skip the lines of most sites and includes premium admission to Shedd Aquarium, Willis Tower, the Art Institute of Chicago, and the Field Museum.