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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.

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