City Guides

10 Festive Things to Do in Chicago This Fall

Kacey Mya
January 16, 2024

As the weather starts to cool down and the leaves begin to fade from green to orange, everyday life is going to change a bit too. People are beginning to embrace the season of fall again, changing everything from drink flavors to outfit choices to fit right along with the changing time of year.

Like all over the world, Chicago celebrates fall with events and things for people to do all around the city. Whether you’re visiting for a short time or live in the city all year round, fall is a great time to look for something fun to do on a breezy afternoon.

Even if you’ve lived in Chicago for a long time, it’s good to be refreshed about festive things you can do in the city. Things are always changing, so you may find something exciting and new you’d enjoy. Read on for a little inspiration for festive things you can do in Chicago this fall, and then get out a pen and paper so you can get started on making your seasonal bucket list.


1. Architecture River Cruise

Combine a fun activity with learning to get to know Chicago better while having fun at the same time. The Architecture River Cruise is the perfect way to do that, especially when the fall temperatures will be just right to be out on the river. As you cruise past major buildings, you’ll learn about their history and fun facts about the city.


2. Bobby’s Bike Hike

For something fun to do with the family, try Bobby’s Bike Hike. It’ll solve the problem of having something do while also letting your kids get their energy out before bedtime. You’ll get a bike tour all around the city, seeing famous locations like the Gold Coast neighborhood and Oak Street Beach. You can stop at any restaurant or bakery you see, plus bars that feature local craft beers you won’t be able to get anywhere else.

3. Bengtson’s Pumpkin Farm

Halloween is one of the best parts about fall, but not everyone likes to be scared. In Chicago, you can still enjoy a trip to an old barn without worrying about anyone getting too scared. The Bengtson’s Pumpkin Farm has pig races, a petting zoo and even rides for the kids. It’s sure to make for a busy and fun afternoon for the whole family.

4. Konow’s Corn Maze

Another great fall activity is getting to explore a corn maze, but don’t think you’ll miss out on it just because you’re in a big city! Konow’s Corn Maze has corn pits, gem mining, and a playland that kids will love. Their maze is miles long, so you’ll easily be able to spend a Saturday figuring out the maze and having fun at their other events.

5. Sonny Acres Farm

A fun way to spend your time in the fall is by picking out a great pumpkin and carving your favorite design into it. The Sonny Acres Farm is sure to have the pumpkin you’re looking for. They’ll also have wagon rides, snacks and a spinning tunnel so you can have some fun before you settle down to carve your pumpkin back at home.

6. Night of 1,000 Jack-o’-Lanterns

The Chicago Botanic Garden knows that when people think of a garden, they’ll picture springtime, so they offer plenty of events in the fall too. One of their most popular is Night of 1,000 Jack-o’-Lanterns. You can take an evening stroll amongst the 1,000 pumpkins that will be glowing with artwork. Snack and drinks are provided, plus a meet and greet with spooky characters and even live carving shows. You won’t be able to leave without being inspired to go home and create a new carving of your own.

7. Naperville Oktoberfest

No October would be complete without an Oktoberfest celebration. You can catch one in the heart of Germantown in Naperville. There’ll be live music on every street corner, from modern hits to classic German folk music. Taste German snacks and beer or visit local food trucks to try something new to the area. There’s fun for family and friends at Oktoberfest without having to spend a bunch of money to attend.

8. Lincoln Avenue Apple Fest

Apples are another traditional fall food and there are festivals around the world incorporating them during the fall. On Lincoln Avenue, you’ll be able to find the Apple Festival. There will be endless varieties of apple pies to try, plus cider and other desserts. Local musicians will come out to play and the kids’ zone will be all set up for face painting and carnival rides.

9. Chicago International Film Festival

It’s no secret that Chicago has been home to many film, television and theater stars, so the Chicago International Film Festival has a special place in hearts all over the world. People travel every fall to see 150 short and full-length films from 50 different countries. Afterwards, you can engage in panel discussions and even attend the opening night party. Any film junkie couldn’t pass this up if you’ll be in Chicago in the fall.


10. The Realm of Terror Haunted House

There are traditional haunted houses and then there’s the Realm of Terror Haunted House. For those who indulge in their spookier side during the fall, you must check out this haunted attraction. You’ll walk through immersive environments and be thoroughly creeped out from the moment you drive into the parking lot until the moment you’re back on the road. Featured in countless magazines and newspapers, this is one of the best fall attractions Chicago has to offer.

During the fall season, you’ll have plenty of activities and events to choose from when you’re looking to fill in your free time. Chicago has lots to investigate, from corn mazes to craft beer biking tours. Whatever fall themed adventure lights your interest, you’re bound to have a season of fun in Chicago this fall.

U30X Chicago Travel Community

Live in the Chicago-area? Join our community of alumni and travel lovers at one of our meetups! We're hosting a Halloween meetup at Moxy Chicago on October, 25th. Come on out and see us!

Kacey Mya
Kacey is a lifestyle blogger for The Drifter Collective, an eclectic lifestyle blog that expresses various forms of style through the influence of culture and the world around us. Kacey graduated with a degree in Communications while working for a lifestyle magazine. She has been able to fully embrace herself with the knowledge of nature, the power of exploring other locations and cultures, all while portraying her love for the world around her through her visually pleasing, culturally embracing and inspiring posts. Follow Kacey on Twitter and subscribe to her blog to keep up with her travels and inspiring posts!


last minute deals


As Seen In...