llinois and the Midwest are really magical this time of year, with the leaves changing colors and beautiful sunsets. Here are some ways to take in the season:
Apples always taste a little sweeter when you pick your own, yeah? Edward’s Apple Orchard was where I went growing up, but you don’t have to go all the way to the northern border. There are some apple picking places closer to the city.
You can also stay close to home for your yearly pumpkin picking. Jack’s Pumpkin Pop-Up in West Town brings the farm to you! Plus, axe throwing, a corn maze and food trucks!
Take in the scenic views along the Mighty Mississippi with an itinerary that includes hot air balloons, wineries, hiking, and more from the Illinois tourism office.
The Best Fall Festivities as leaves turn orange

Sidney Madden

City Cast's Carrie Shepherd at Edward's Apple Orchard in Poplar Grove. (Provided)
Share article

Stay connected to City Cast Chicago and get ready to join the local conversation.
Chicago's Best
Hidden Gem Swimming Spots
Underrated swimming spots in Chicago this Summer.
5 Queer Chicago Poets You Should Know
These local queer poets are worth checking out — during Pride month and beyond.
Welcome to The Belmont and Decibel — AKA New Berlin
Decibel is now open in the former Berlin space on Belmont. Comparisons are inevitable.
Chicago Was — Is? — a Magic Town
The Hand & The Eye is a new venue marketing Chicago-style magic. But what is Chicago-style magic?
Chicago’s Splashiest Water Activities
As we mourn the Humboldt Park swan boats, there are still plenty of Chicago water and boat activities to enjoy as the season heats up.
Celebrate Poetry in Chicago
Every month is Poetry Month in Chicago. But since April is actually National Poetry Month, consider diving in deeper.
Where You Can Still Bowl in Chicago
There are just about a dozen bowling alleys left in Chicago. Lucky for us, though, they’re as fun as ever.
Your Guide to April 2026
April showers bring May flowers. But this month has a lot more than just rain, check out everything to do in Chicago!
The latest in Chicago
Take This Week's Chicago News Trivia Quiz
How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.
Explore Chicago’s Indigenous History
Chicago has always been a Native place. See which nations call it home and the real story behind its name through the Indigenous Chicago...
Your Guide to Chicago’s Indigenous-Owned Businesses and Organizations
Support Chicago's Indigenous community and catch a dance and drum show, enjoy Indigenous cuisine, view Indigenous Futurist art, and learn...
🎃 Your guide to October
A full guide on how to make the most of October in Chicago.
Where To Find Chicago’s Crafting Community
Want to connect with other fiber craft enthusiasts? Here are a few groups of sewing enthusiasts and makers who meet around Chicago.
Your Guide to Fiber Crafts in Chicago
Here's a roundup of local shops that have everything you need to start your next project, plus workshops where you can learn new techniques.
‘Tis the Season of Film Festivals
Here are the film festivals in Chicago that you won't want to miss in September and October 2026.
Your Guide to Chicago’s Indie Theaters
Ditch the megaplex and check out this guide to our favorite indie and historic movie theaters in Chicago.

