September 2023: As we transition from summer to fall, it's time to start thinking about the season ahead. This month, we're heading out to suburban orchards to go apple picking and checking out a pumpkin patch pop-up in the middle of the city. Football season is also here, but you still have some warm days for rooftop drinking, kayaking and boat cruises. There are plenty of food and drink options, too, so stay satisfied and busy with these fun activities in 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 50 best things to do in the world right now.