Looking for the best things to do in October in Chicago? This is the guide for you!
Chicago is one of my favorite cities in the entire world, and the city has a whole new ambiance when it comes to spooky season.
I visit several times every fall and have curated a list with some of my favorite fall activities unique to October!
I didn’t think I could love Chicago’s skyline views anymore, but apparently, throwing pumpkins and twinkle lights into the mix gives me a whole new reason to love fall.
Some of the best things to do in October in Chicago include Riverwalk party, Chicago Riverwalk, Lincoln Park Fall Fest, Open House Chicago, Oktoberfest, Chicago Marathon, JoJo’s Shake Pumpkin Patch, Jack’s Pumpkin Pop-up, and fall foliage.
10 Fall Things To Do in Chicago
1. Fall Fest on The Riverwalk
The Riverwalk party officially features my favorite fall views of Chicago!
The party has outdoor games like bags, live band entertainment throughout the day, and food and drinks for purchase.
In 2024, you could purchase Earlybird tickets through Eventbrite for as low as $5. At the door, ticket prices increased to $25, so I highly recommend purchasing in advance.
Tip: Enjoy the live music for free by sitting on a bench along Chicago’s Riverwalk.
2. Chicago Riverwalk
The Chicago Riverwalk is one of my favorite Chicago activities and I recommend it on any Chicago itinerary, but there’s extra reason to visit in October.
Every October, the riverwalk is decorated with seasonal fall displays like hay barrels and pumpkins.
It’s convenient to stroll the riverwalk on the way to any other Chicago events and is right at the launching point for Chicago boating activities like the famous Architecture Cruise.
The architecture cruise is one of the most popular tours in Chicago and runs year-round.
3. JoJo’s Pumpkin Patch
JoJo’s Shake Bar is known for their full-out dessert milkshakes in the summer and hot cocoa in the winter. Recently, the shake bar has become even more famous for its seasonal, on-site pumpkin patch.
It’s small, but I definitely recommend it. There are plenty of photo ops from red tractors to a huge wall lined with pumpkins.
You can make reservations online in advance, but there were plenty of open tables during my weekend visit in October.
It’s a great fall Chicago activity for all ages.
4. Lincoln Park Fall Fest
Fall Fest is a free Fall party on the Lincoln Park trail.
Other neighborhood fall events include:
- Chicago Fall Fest
- Lincoln Square Apple Fest
- Arts in the Dark Parade (Chicago Loop)
5. Open House Chicago
Open House Chicago is an annual city event held in October each year.
This favorite activity among locals allows visits to famous Chicago buildings, otherwise closed to the public.
6. Oktoberfest
Several Oktoberfests pop up in the city every fall.
This event, with origins from the traditional Oktoberfest in Germany, is a popular fall festival that you can find in several neighborhoods.
Visitors can enjoy authentic German beer and cuisine, with bratwurst and pretzels being among the crowd favorites.
The festivities usually include live polka music and dancing, adding to the lively and festive atmosphere.
⭐More Chicago Seasonal Guides
7. Chicago Marathon
Have you ever witnessed an international marathon?
Watching my friend run the Chicago Marathon last year was probably one of my favorite experiences ever.
You can volunteer to work at the marathon, register to run, or spectate and cheer as the dedicated runners take to the streets of Chicago.
Tip: Hotel prices will be extra high the weekend of the marathon.
I highly recommend tracking for cheap prices well in advance if you are planning on visiting during the event.
8. Rooftop Cinema Club
Chicago’s Rooftop Cinema Club is the only outdoor, rooftop movie theater in the city.
Located in Chicago’s popular Fulton Market neighborhood near West Loop, there are tons of shopping, restaurants, and things to do all around you.
The Rooftop Cinema Club closes for the season on October 31st.
9. Fall Foliage
Finding the best fall foliage in Chicago is like going on a treasure hunt. I love finding the rainbow leaves in Chicago’s amazing green spaces.
Some of the best include rainbow ivy draped across Chicago’s historic University of Chicago campus (feels like a Hogwarts experience).
You can find even more rainbow foliage in places to hike near Chicago like Starved Rock or Indiana Dunes.
Read Next: Best Midwest Fall Foliage
10. Chicago Skydeck
Looking out over the city from the Chicago Skydeck is one of the best Chicago panoramic views I have ever experienced! Seeing the city from this high above is something specatcular- and imagine it from a glass ledge!
I mean, WOW. I recommend visiting on a clear day with minimal cloud coverage for the best views. The experience on the ledge itself is one minute and a half but you can continue entering the line to experience it again. You can stay on the top floor of the building admiring the views for as long as you would like.
Conclusion
Chicago features tons of amazing fall events and activities every October.
From the rooftops to urban fall parties, Chicago offers something for everyone in October.
As an expert on Chicago’s local scene, I know that these activities will enrich your city experience!
Don’t let the Fall pass by without diving into all that Chicago has to offer—start planning your perfect fall adventure now!
