Must-Do Experiences in Chicago
Collected by Kaitlyn Barrett, AFAR Local Expert
There are hundreds of reasons to love Chicago, and iconic architecture, laugh-a-minute comedy shows, world class art, and deep-dish pizza top that list of must-do experiences. A Cubs game with a Chicago dawg at Wrigley Field is a classic Chicago experience, as is the musical festival Lollapalooza. Visitors to Chicago should make time for the Willis Tower skydeck, with its aerial views of the city, and the glittering expanse of Lake Michigan.
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
26 W Randolph St, Chicago, IL 60601, USA
A combination of sugar and salt, sweet and savory, there's nothing like Garrett's "Chicago Mix"—a combination of caramel corn and cheese popcorn. It's the kind of thing I crave in such a way that it's a good thing I don't live in Chicago....
1616 N Wells St, Chicago, IL 60614, USA
The Second City has come a long way since the small cabaret theater that launched in 1959. As a sketch comedy and improvisational performance theater, the venue has been keeping people laughing for over 50 years. Situated in the historic Old Town...
6836 N Sheridan Rd, Chicago, IL 60626, USA
Ask any local where to try your first real deep-dish pizza and they'll say "Giordanos." It's obviously the best in town. Chicago-style pizza is unique and totally different than what you'll find in Italy. More like a pie, the crust is tall and...
111 S Michigan Ave, Chicago, IL 60603, USA
Just imagine having 264,000 square-feet of modern art at your disposal seven days a week. That is exactly what you have if you visit the Modern Wing of the Art Institute of Chicago. Above is but one example of the funky-cool exhibits that await...
337 E Randolph St, Chicago, IL 60601, USA
I know, I know, Lollapalooza may be a little overpriced and overrated. But the truth is, it is still one of the best music festivals in the country. Amazing live performances by well-known artists and new talents, worldwide travellers, a quirky...
Streeterville, Chicago, IL 60611, USA
The architectural boat tour of downtown Chicago is the single best way to see this city in a whole new way. From first-timers to lifers, it doesn't matter how long you've been in town, this perspective is going to be new to all. There are many...
Illinois Medical District, Chicago, IL, USA
Chicago is the king of comedy, hot dogs, and extreme Midwest weather. But since the Great Chicago Fire of 1871, the city has been reinventing itself. Today, clever design projects (such as “Color Jam,” shown) top the list of reasons...
1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to...
201 E Randolph St, Chicago, IL 60602, USA
The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife's favorite quote, and a local sight in Chicago. Sometimes people feel they...
112 E Upper Wacker Dr, Chicago, IL 60601, USA
The Chicago River and Lake Michigan are two of the city’s greatest assets, and there’s no better way to experience both than with an architectural boat tour. While there are plenty of reliable options around, go with First Lady...
2007 W Churchill St, Chicago, IL 60647, USA
Rising nearly 18 feet above street level, the 606 (which takes its name from the common numerals in all Chicago zip codes) serves as a 2.7-mile elevated park and trailway for cyclists and runners, while also connecting neighborhoods...
- 1 Expat Life 11 Best Islands to Move to After Retiring
- 2 Air Travel Another U.S. Airport Now Allows Non-Ticketed Visitors Through Security
- 3 Travel News Why You Should Go to New York City This Winter
- 4 Holiday Travel 15 Go-to Pieces of Travel Gear to Gift This Holiday Season
- 5 Where to Go in Winter 12 Great Beaches for Winter Sun