13 Things To Do For Halloween In Chicago If You Haven’t Made Plans Because Life Is Scary Enough - Chicago - The Infatuation (2024)

Fall in Chicago is full of plenty of things to look forward to: sweater weather, piles of crisp, colorful leaves, and the opportunity to dress like a “sexy pumpkin” if you so choose. It also means all sorts of Halloween activities. Whether you’re in the mood for a haunted history tour or want to see some scary movies at a drive-in, here are some fun things to do in Chicago this fall.

This is a rolling list, so check back for updates. And if you want to get out of the city, here's Where To Do Fall Stuff Within 90 Minutes Of Chicago.

THE HALLOWEEN THINGS

Time Out Market in Fulton Market will be turning all three of its floors into an immersive Death By Disco party on October 26th. There will also be 15+ DJs and three stages. While you’re there, you can check out their selection of food stalls like Bar Goa, Demera, and QXY Dumplings.

Logan Square’s Emporium is hosting a pop-up market called Halloween Hangout on October 18th and 19th. There will be music, movies, a costume contest, food, and horror-themed artwork available for purchase.

With over 10,000 pumpkins as part of its setup, Jack’s Pumpkin Pop-up in Goose Island is the largest pumpkin-themed installation in Chicago—a thing we didn’t realize was being measured until now. But aside from having an absurd amount of the season’s most popular squash, they also have food trucks, carnival games, bars, and a massive corn maze.

If you’re looking for both caffeine and some scary movie inspiration, stop by The Brewed in Avondale. The space is decorated in all sorts of vintage horror-themed memorabilia, with plenty of old-school movie posters and tchotchkes.

And if you still can’t think of anything to watch after visiting The Brewed, you can always just pop into Whiskey Business in Wicker Park. Until the 27th of this month, they’re hosting a Buffy the Vampire Slayer pop-up, with a special drink and food menu. Click here for more information.

This October, The Music Box Theatre is hosting a horror movie series called Music Box Of Horrors: The Dream Child. Every night, you can expect a wide range of scary movies from classics like The Exorcist III to newer cult favorites like House Of The Devil. Get tickets and check out the full lineup here. And on the 25th, 26th, 30th, and 31st of October, they’ll be doing special presentations of Rocky Horror Picture Show.

For a theater experience that doesn't require looking for street parking, you can catch a drive-in movie at Chitown Movies in Pilsen. Tickets for their line-up of movies like Grease, Beetlejuice, and the original Halloween can be found here.

Lincoln Park Zoo is hosting a wide variety of events as part of their annual Fall Fest. Haunted history tours take place every Tuesday and Wednesday, and for a less spooky way to see the zoo, there are fall garden tours every Friday at 10am. On October 19th, they’re hosting Spooky Zoo, a day where kids can show up in costume and trick-or-treat while checking out the animals. They also have a few scheduled events like "Adult’s Night Out" on Thursday, October 24, with free rides on the Giant Fun Slide, a DJ, and a cash bar.

Navigating the hordes of tourists at Navy Pier already feels like a scene from The Walking Dead, so a trip here during the Halloween season already makes sense. Plus, on October 26th, they’ll host Slightly Spooky Saturday. The pier will be ready for trick-or-treating throughout, and there will be festive activities like axe-throwing and live performances. Be sure to check their website for updates.

This October, Replay in Lincoln Park will host a “Nick Or Treat” pop-up filled with ‘90s TV childhood nostalgia. Along with Replay’s usual free arcade games, there will be themed drinks, trivia, events, and more. Click here for more information.

During this two-hour, pay-what-you-like walking tour in the Loop, not only can you explore the city before sidewalks are covered in slush, but you can also learn about some of Chicago’s local haunts. Chicago’s Ghost Tour covers a wide variety of weird downtown history, from the hauntings at the Congress Plaza Hotel to Death Alley to the alleged SS Eastland ghosts along the river. You can book your reservation here.

For a bar crawl with extra scariness (besides realizing that you left your card at the bar), book a tour with Nightly Spirits in Lincoln Park. This walking tour covers some of Chicago’s haunted history, including stories about gangsters like Dillinger and Capone while stopping by neighborhood bars along the way.

Even if you’re not necessarily into nerding out about flying buttresses and the beaux-arts style,The Architectural Boat Tour is still one of the most unique ways to see the city. For an hour and half, you’ll learn some history, see some great views of the buildings and the changing colors of the leaves, plus every boat has a bar if you’re in the mood for a drink. Tickets and departure times can be found here.