We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than 15 kitchens, three bars, one drop-dead gorgeous rooftop terrace and a host of events—all spread across three floors.
September 2025: Is that a chill in the air we feel? The warm embrace of pumpkin spice we smell? The sound of leaves crunching beneath our feet? Ah, yes, fall is descending upon Chicago. September brings with it some of Chicago’s finest seasonal events, from Taste of Chicago and Riot Fest to the Ravenswood ArtWalk and the World Music Festival. If you’re eager to raise a stein and chow down on some schnitzel, we’ve rounded up some of the city’s best Oktoberfest events, too. Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September.
No matter where your interests lie, you can always find something to get excited about in this no-nonsense Midwestern metropolis. The best things to do in Chicago run the gamut—from seriously fun to awesomely educational. Looking for culture? Spend a day exploring Chicago museums. Hungry? You've come to the right place, because Chicago is famous for its delicious cuisine. There are tons of amazing restaurants in Chicago that highlight the city's rich and diverse culinary landscape. (And plenty of uniquely Chicago bars that do the trick, too.) We've searched all across the city to assemble this list of the best things to do in Chicago. Follow it and never get bored here again.
You can also find out more about how Time Out selects the very best things to do all over the world, or take a look at our list of the best things to do in the world right now.
RECOMMENDED: Check out Time Out's interactive map of the best things to do in Chicago