Voted the Best Big City in the U.S. for the fifth year in a row by Conde Nast Traveler readers, Chicago is ready to welcome you!
No matter what you call it – Chi-Town, The Windy City, The Second City – this city of nearly 3 million inhabitants is a celebrated melting pot, offering hundreds of film festivals, music festivals, dance troupes, theatres, live music venues and more. Take some time to explore the city’s arts and famed architecture.
Chicago is also a foodie destination, with:
- More than 7,300 restaurants
- 80 Michelin-starred and Bib Gourmand restaurants
- 40 James Beard Award-winning restaurants
- 84 three-, four- and five- Diamond AAA-rated restaurants
Laugh, Cry and Fill Your Belly
With a famous Broadway musical named Chicago, it’s a given that the Windy City will have a vibrant and bustling theater district and performing arts scene.
The Chicago Theatre District is located in the heart of downtown, and is a hub to watch world-class productions and premieres like 3-time Tony Award winner Wicked. Or if you prefer to laugh the night away at a comedy club, catch a show at The Second City and see where Bill Murray and Tina Fey practiced their punchlines. No matter where you start, end your night at one of the many theater district restaurants. You can’t go wrong with a dinner and a show!
History, From Architecture to Al Capone and Speakeasies
Sure, you have seen the famed Willis Tower (formerly Sears Tower), but did you know the first skyscraper in the world was built in Chicago? In your down time, why not learn more about the rich history of the Windy City? Travel through time on this walking tour that covers Chicago's most famous buildings in chronological order. Or learn about the architectural heritage of the exquisite skyline while cruising down the Chicago River.
Once home to ruthless gangsters like Al Capone, visit Chicago’s mafia past with a crime tour detailing the mob history during the Prohibition era. Or put on your pinstripe suit and fedora hat and grab a cocktail at one of the city’s hidden speakeasies.
Sunsets, Ghosts and All That Jazz
With so many choices, figuring out what to do this Fall in Chicago can be overwhelming, so we narrowed a few options down for you!
If sightseeing is what you’re after, enjoy the city’s breathtaking architecture drenched in golden sunlight on a sunset evening river cruise. With Halloween just around the corner, why not try a Chicago ghost tour and see if some of those haunted urban legends are true. After visiting the world famous museums and parks, check out the night life and catch a show at one of the many rocking music venues like Andy’s Jazz Club.
A Game of "Operation" Gone Wrong?
You may have been impressed after visiting the iconic Art Institute of Chicago and Field Museum, but did you know about the International Museum of Surgical Science? Housing a collection of artifacts and exhibits that document the history of surgery, it is a must-see for anyone interested in the history of medicine. It has also been described as a game of Operation gone wrong, so it’s not for the squeamish.
If you prefer to go off the beaten path, there is a plethora of unique and unusual activities. Visit the Woolly Mammoth Antiques and Oddities curiosity shop to sift through some animal bones and human teeth. Or try turtle racing at Big Joe’s on a Friday night. The more drinks you buy, the more tickets you get.
Admittedly this is not for everyone. If you are curious but too intimidated to venture out by yourself, there is a Weird Chicago Tour to help you navigate it all. Have fun!
Explore Chicago’s Fall Beauty
After enjoying WCC VIII, get outside, stretch your legs, and explore the beauty of Chicago in the Fall.
Start your day by grabbing a cup from one of Chicago’s premier coffee shops, and then head over to Lincoln Park to see the beautiful red and gold fall foliage. You can also check out many other attractions while there, such as the Lincoln Park Zoo or Chicago History Museum.
Take advantage of the pleasant Autumn weather and book an architecture river cruise highlighting the Windy City’s architectural experimentation and innovation. At this point, you will be famished, so make sure to grab a famed Chicago deep dish pizza at Giordano’s. End your night at a rooftop bar with sweeping city views. Don’t forget to impress your friends with your new Chicago knowledge while sipping your fancy cocktail.
Get a Bird’s-Eye View of Chicago
Have a couple days before or after WCC VIII and AAO 2022? Spend them exploring the stunning architecture, vibrant neighborhoods, and award-winning restaurants of Chicago.
Catch your reflection in “The Bean” at Millennium Park, the lakefront park in Chicago's downtown Loop. After enjoying the skyline views from below, try seeing the iconic skyscrapers from a different perspective. View the city from over 1,000 feet in the air inside The Ledge’s glass viewing platform. With 23 restaurants anointed with Michelin stars, don’t forget to check out the fine dining scene. Try one of this year’s newcomers Esme or Galit.
Sports or Museums? Chicago’s Got the Best of Both
From the Bulls to the Bears to the Cubs, Chicago is one of the top sports cities in the U.S., attracting fans from all over the world. Soak up the atmosphere at a Bears game, or book a tour of historic Wrigley Field, the second-oldest MLB ballpark in the nation. Or watch your favorite team with your drink of choice at the many lively bars and pubs.
If art is more your thing, visit one of the many museums, unique art galleries, or vibrant art districts Chicago has to offer. Whether you are checking out the ancient Egypt exhibit at the Art Institute of Chicago, or jumping into the pool of sprinkles at the Museum of Ice Cream, there is something for everyone.
With so many educational sessions and events, you may need a minute to catch your breath and unwind. Relax your retinas at one of Chicago’s best luxurious day spas. Try a vintage bourbon massage at the Four Seasons Hotel or Chuan Spa’s Jet Lag Revival, designed to combat fatigue and mental exhaustion.
If you’d like something a bit more active, find your zen at a yoga studio, or try a leisurely walking tour taking in the famous industrial landscape along the Riverwalk. Don’t forget to grab a bite at one of the many iconic restaurants like the Berghoff, sprinkled throughout the city. You will be refreshed and recharged in no time.
See what’s happening at Choose Chicago.