City Cast Chicago logo
Display Ad: Children play near Chicago's Cloud Gate. "Big plans. Coming right up." with pizza graphic on left; "Enjoy Illinois. Meet in the middle." on right.

Your Guide to Chicago in October 2025

Posted on October 1, 2025
Emily Mack

Emily Mack

Hot dog Halloween costume

A fellow hot dog lover on Halloween … but why are there ketchup bottles in his wheels?! (Photo by Bilgin S. Sasmaz/Anadolu Agency/Getty Images)

Halloween season is upon us — we’ve got you covered on events all month long. But that’s not all that’s coming up in Chicago.

Podcast Player: "Your Guide to October 2025 in Chicago"

Halloween in Chicago

I love Halloween. This year, I’m going as either a hot dog “dragged” through the garden or Captain Jack Sparrow. Keep checking Hey Chicago: Additional costume ideas, spooky cemetery stories, and haunted house recs are coming soon 👀

In the meantime, plan your Halloween by snagging party tickets early. Spooky events this season include:

Leaf-Peeping Season

The Midwest is beautiful this time of year. Take a day trip for a full fall experience, maybe driving out to Apple Holler or Alton, Illinois, “America’s Most Haunted Small Town.” Or hop on the Metra!

Then again, you don’t need to leave the city to see amazing fall foliage. My personal recommendation is the North Park Village Nature Center, which has its annual Fall Festival — and scarecrow-making contest — on Oct. 19.

Sports? Sure!

I don’t follow sports closely, but even I know the Cubs are in the playoffs. They’re playing the Padres Thursday. Wrigleyville has been feeling the hype all season.

You can now watch games live at Babe’s, a new sports bar in Logan Square. But don’t expect to see the Cubs there. This rosy-hued den is for women’s sports only!

Vaccination Reminder

Despite waning federal mandates, Illinois’ vaccine panel recommends people get their COVID-19 vaccine and a flu shot — and that young kids get RSV vaccines. This is especially important as respiratory virus season picks up.

Free walk-in appointments for flu and COVID-19 vaccines are available at four clinics. Appointments for individuals 12 and older will be available at more city clinics starting Oct. 6.

Affy Tapple donuts from Stan’s

The Affy Tapple donuts from Stan’s. (Courtesy of Page One Public Relations)

Seasonal Donuts

It’s apple cider donut season! Personally, my favorite ones come from Didier Farms out in Lincolnshire. Perhaps a bit closer to home, Firecakes carries the cinnamon-y fall delicacy.

For those with an even sweeter sweet tooth: The Affy Tapple x Stan’s Donuts collab is back at all Chicagoland Stan’s locations through Oct. 31.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.
Advertisement image

The latest in Chicago

Neighborhood GuidesApril 23

Where to Read in Chicago

It’s National Library Week through April 25 — which is coincidentally Independent Bookstore Day! There’s an official crawl across Chicago...

A white building with pillars, on the street there are cars parked in front of it
Chicago, ExplainedApril 22

The End of an Era For Lincolnwood Town Center

Lincolnwood Town Center shuts down April 30 — depending who you ask. I went to the mall to check things out for myself.

Emmi Mack at Lincolnwood mall
Neighborhood GuidesApril 20

Celebrate 420 at These Chicago Dispensaries

It’s been a little over 6 years since recreational marijuana was legalized in Illinois. At the time, Gov. JB Pritzker called it the “most...

Three people standing in a room. In the back is art work. There are 4 paintings across, and 3 paintings down
Chicago, ExplainedApril 17

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events? Test yourself in our weekly trivia quiz.

A security officer and his dog at a CTA Blue Line Station
3 Questions WithApril 14

3 Questions With Chicago’s Poet Laureate

It’s National Poetry Month, and while you can find a variety of workshops and open mics in April, poets call Chicago home all year round.

A woman smiling while sitting. There is a potted plant in the back
Chicago HistoryApril 8

Who’s Preserving Chicago Family History?

If you are like me, all your family history lives within multiple photo albums and VHS tapes stored in your parents’ living room cabinets.

Group of adults and children sit in a circle around an infant lying down in a home
Food & DrinkApril 6

New Spots To Dine & Drink in Chicago

Chicago has no shortage of good places to eat around town. Here are some of the bar, restaurant, and café openings we're watching.

Chef Jake Schneider of Schneider Deli
Food & DrinkMarch 30

Hot Chicken in Chicago

Chicago has plenty of its own famous sandwiches, but the Nashville hot chicken trend is still going strong across the city.

Woman holds hot chicken sandwich in front of pink wall featuring large painted illustration of a chicken