Danielle Jeanjaquet
The fall season is one of the best times to visit Chicago!
The weather is just chilly enough for cozy fall sweaters, but still warm enough to run around the city.
And, the fall foliage is especially beautiful in this part of the country, with all Chicago’s trees turning orange, red, and yellow.
There’s also tons of fall events to explore and yummy eats to try!
This list of fun Chicago activities to do in fall will gear you up for an amazing visit (or staycation) in the Windy City.
Let’s jump in with one of Chicago’s amazing fall food festivals!
#1. Apple Fest
The Lincoln Square Ravenswood Apple Fest is an annual event where dozens of local vendors come together on the streets of Chicago to sell delicious fall foods and craft items.
There are apple products everywhere you look! You can grab a huge bite of Chopping Block’s fresh apple pie, and some cozy apple cider to drink with it.
Candy apples, apple empanadas, and apple cinnamon donuts were some yummy treats I got to taste when I was there!
They also have lots of clothing items and artisan goods you can buy from the local shops, like scarves, spices, and candles.
Live music is a big part of Apple Fest as well, with choirs, bands, and singers performing all weekend.
#2. Fall at Chicago’s Lincoln Park Zoo
You’ll also find a Fall Fest at Chicago’s Lincoln Park Zoo!
This event is free and runs all through October. Explore the zoo for no cost and enjoy all the animal exhibits while checking out the fall decorations and special events.
There’s lots of ticketed activities for families, like a ferris wheel, slides, an obstacle course, and more!
Adults can have plenty of fun too, with the corn maze, live music, and the pumpkin patch.
#3. Explore Lincoln Park
After enjoying the fall events at the zoo, you might want to explore the Chicago fall foliage in Lincoln Park!
Lincoln Park is quite massive, but the walking paths near the zoo provide some lovely views of the city and its fall colors. You might stroll through the conservatory gardens or on the nature boardwalk. There are some amazing views of Chicago’s skyline from these areas!
Both North Pond and South Pond in Lincoln Park also offer some picturesque nature sanctuaries and have plenty of autumn foliage to enjoy. While South Pond is closer to downtown Chicago, North Pond also hosts a swanky restaurant where you can stop by for dinner or Sunday brunch.
You can even head over to the Lake Michigan beaches if you’d like! The crisp fall breeze might be a little chilly, but the North Avenue Beach offers some of the best views of Chicago and the lakefront.
#4. Chicago International Film Festival
For an indoor fall activity, you might check out Chicago’s International Film Festival. It’s an annual event that lasts about a week and a half every October.
It holds the record for the longest-running competitive film festival in North America, and offers world-class cinema from the industry’s leading and upcoming professionals.
You’re sure to find all sorts of original, new-age films from countries all over the world! You can buy a pass for a part of the festival, or you might pay single-ticket price to enjoy just one film that seems interesting to you.
#5. Haunted Chicago Tour
If you love spooky stories and history, then taking a haunted tour of Chicago might be the perfect fall activity for you!
Weird Chicago Tours offers both group tours and private sessions, either by foot or by bus. Their ‘Haunted History’ and ‘Devil & The White City’ tours are some of their most famous ones!
Nightly Spirits also gives a Haunted Ghost Tour & Pub Crawl. It’s a walking tour that explores some of the most legendary ghosts and gangsters from Chicago’s prohibition era.
For a tour that doesn’t require as much exercise, you might check out the Absolutely Chicago Segway haunted tour. You can enjoy the nighttime sights of Chicago on a segway, gliding around town to hear all about the city’s scariest ghost tales and disasters.
#6. Comedy Show at Second City
Another way to spend fall in Chicago is at The Second City. Second City is an improvisation and comedy theatre troupe and school that puts on some fabulous productions in Chicago.
They also like to celebrate fall with some Halloween-themed shows, such as their Trick ‘n Treat Yourself Improv or the Halloween Spooktacular! You’re sure to have a laugh at these spooky improv or sketch-comedy shows.
#7. Chicago’s Oktoberfest
Chicago is a great place to celebrate Oktoberfest!
Check out Chicago’s German-American Fest in Lincoln Square. Or, take a boat ride on the Chicago River with Shoreline Sightseeing’s Oktoberfest Cruise.
Lots of Chicago breweries and restaurants get into the fall spirit as well with hearty German beers and eats.
Funkenhausen has affordable happy hour specials, The Gage offers eclectic food and drink pairings, and Prost! is a German beer hall with lovely outdoor garden seating.
That’s all for my fall in Chicago recommendations!
What fun things do you like to do in Chicago during Autumn?
Let me know if you try any of these events out in the comments below!
