If you have a trip planned for Chicago in the fall and are looking for seasonal activities to enjoy, you’ve come to the right place! Chicago is worth visiting any time of year (although beware of the brutal winters), but I wanted to focus on what to do if you’re here in September, October, or November. This post was inspired by a ghost tour my boyfriend and I just did, which would be so perfect during spooky season.
I came up with nine other autumnal ideas to give you a list of ten to choose from–that just felt right! Of course you can’t go wrong with an architecture tour, sporting events, museums, deep dish pizza, or taking pictures with “The Bean.” The recommendations in this post should be add ons to all the great things the Windy City has to offer year round!
When thinking of what to include in this list of 10 things to do in Chicago in the fall, I was inspired by halloween candy, Oktoberfest, falling leaves, pumpkins, apple cider, witches, haunted houses– all the things we associate with this season. I have personally done six out of these ten and can vouch for them from experience. The other four are still on my Chicago bucket list, and I can’t wait to do them later this year 🙂 So let’s get into it!
*gifted: 2 tickets from US Ghost Adventures. all thoughts are my own.*
One. Ghost Tour
Let’s start with the activity that inspired this whole post! I had been wanting to do a ghost tour of Chicago for the longest time. Walking tours in general are such a great way to get a feel for a city, and the niche ones are especially fun. Chicago has a dark history that was really interesting to learn more about while strolling around Lincoln Park. You’ll hear about cemeteries, the first man wanted by the FBI, and lots of ghosts! We were super spooked by the end of it and even captured this haunting photo walking back to our car…
Link: Windy City Ghosts
Two. Jack’s Pumpkin Pop Up
If you want a plethora of fall photos, look no further than Jack’s Pumpkin Pop Up. I went with some girlfriends a couple years ago, and we had so much fun taking ALL the pictures, throwing axes, and enjoying seasonal drinks. Awesome way to get in the fall spirit!
Three. Morton Arboretum
The day we went to the Morton Arboretum was my favorite day of 2023. So although this spot is about a 30 minute drive from the city, it’s soooo worth it if you have a car. And there is no better season to visit than autumn. You have miles and miles of trails to walk under the bright oranges, reds, and yellows of the falling leaves. They also have an outdoor art exhibit that changes every two years, so you can make it into an art hunt/hike. It’s the perfect way to appreciate the relationship between nature and art while moving your body and enjoying all the views.
Four. Chicago Flyover Experience
Falling leaves and… virtually falling from the sky over the city? I’ll admit, making this recommendation seasonal was a bit of a stretch, but I had to include it because it’s new and so fun! If your visit to Chicago in the fall includes any bad weather, this is a perfect indoor activity. Flyover is a world class, high tech experience that is only in Chicago, Las Vegas, Vancouver, and Iceland. So it really is a special and unique thing to do that I 10/10 recommend.
I wrote about the Chicago Flyover Experience extensively here if you want more information. And here’s the link to their website.
Five. Orchestral Shows
Chicago has a great Broadway scene, and usually they put on a seasonal performance or two in the fall. For example, in November of 2025, they are doing a Twilight In Concert by candlelight series. How fun would it be to watch that movie with a live orchestra??
On October 25, 2025, the Auditorium Theatre is welcoming the Chicago Philharmonic to perform the music from The Nightmare Before Christmas during the movie. Costumes are encouraged!
If you’re reading this post and those dates have passed, definitely check the websites for Broadway in Chicago, the Auditorium Theatre, and the Chicago Philharmonic. You can see what events they have coming up for your visit.
Six. Chicago Magic Lounge
I’ve been to a magic show in New York City and loved it, but I still need to check out this one in Chicago. When I think of spooky season, magicians and witches and spells definitely come to mind. The Chicago Magic Lounge is a speakeasy located behind a laundromat in the Andersonville neighborhood of the city. I can vouch for the neighborhood, though! I spent my birthday there shopping for books and stationery and art 🙂
Read more about Andersonville here: My bookish birthday haul from 4 spots in Chicago
Seven. Prost!
If you can’t make it to Germany for the real Oktoberfest (I’m going this year ahhh!), you can visit a German beer hall in Chicago in the fall instead. Prost! has traditional food, steins of beer, and lots of sports on TV. It’s actually quite close to where the ghost tour meets in Lincoln Park (about a 15 min walk)… you could easily combine both these ideas into one very seasonal day!
Eight. Drink Cider
To celebrate apple harvest season, head to The Northman Beer & Cider Garden. Sip local ciders while you admire views of the Chicago River. Farm to table alcohol 😛
Nine. Sugar Factory
Nothing says fall more than sifting through piles and piles of Halloween treats. To replicate a similar feeling (plus alcohol), head to Sugar Factory for insane candy inspired cocktails and an on-site sweets shop. It’s giving sugar coma but looks so fun and indulgent!
Ten. County Line Orchard
If you have a car and are willing to drive about an hour to this farm in Indiana, you will be able to have the quintessential fall day. I go every year! County Line Orchard is home to amazing apple cider and pumpkin donuts, apple cider slushies, tractor rides, a corn maze, food trucks, shopping, sunflower picking, a pumpkin patch, and entertainment for kids. Put on your flannels and enjoy all the best things about fall!
Conclusion and Bonus Idea Coming Soon!
So there you have it! Ten seasonal things to do in Chicago in the fall–such an ideal time to visit in my opinion. I wanted to end this post with news from Universal Studios. In 2027, a year-round horror experience is set to open in the city called Universal Horror Unleashed. It will make Chicago an even better place to visit during spooky season!
Quick Links
And finally, I wanted to share some of my favorite hotels that I’ve stayed in and a restaurant I love to round out this post of 10 things to do in Chicago in the fall. That way you can plan the majority of your trip from one article 🙂
Viceroy: super luxe at a reasonable price.
21C Museum Hotel: one of the nicest, most affordable hotels I’ve stayed in that has its own free art museum for guests.
Publishing House Bed and Breakfast: my #1 favorite accommodation in the city. I think about my time here almost daily if I’m being honest–it was that good. I’ve only been once, but I am dying to go back.
Aba: my favorite restaurant in Chicago. Sooooo cute and the food was incredible.
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All the other blogs I’ve written about Chicago 🙂 from a self-care solo weekend to a romantic getaway and even a Christmassy trip if your visit is more in the November-December timeframe.