17 Things To Do For Halloween In Chicago If You Haven’t Made Plans Because Life Is Scary Enough guide image

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17 Things To Do For Halloween In Chicago If You Haven’t Made Plans Because Life Is Scary Enough

Make the most of the weekend with pop-ups, parties, bar crawls, and more.

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 on a rooftop, here are some fun things to do in Chicago this fall. 

This is a rolling list, so check back for updates. In the meantime, read our Ultimate Fall Festival Guide for a list of even more fall activities happening across Chicago. And if you want to get out of the city, here's Where To Do Fall Stuff Within 90 Minutes Of Chicago.

The Infatuation Chicago Guide To Fall 2022

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THE HALLOWEEN THINGS

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From Oct 28-31, Saint Lou’s in the West Loop is swapping out their usual menu for a Waffle House-themed selection of breakfast items. You can expect dishes like hot chicken and waffles, steak and eggs, and poutine hashbrowns.


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Boos and Views is a Halloween party happening on Oct 29th at Cabra in the West Loop. There will be themed cocktails, snacks, a DJ set, dancing, and even a costume contest where you can win up to $700. Get tickets here.


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Time Out Market in Fulton Market is hosting a Día De Los Muertos party on October 29th, with live bands, DJs, a costume contest, and drink specials. While you’re there you can check out their selection of food stalls like Big Kids, Soul and Smoke, or new tasting menu spot Valhalla.


No Tricks All Treats is a pop-up market hosted by Ainslie Arts Plaza that’s happening on October 29th from 11am-4pm. There will be face painting, crafts, complimentary candy, tarot card readings and food and merchandise for sale from local vendors.


If you’ve been meaning to check out The Robey's new tiki bar, Clever Coyote, or their rooftop while the weather is still bearable, you can during Wicker Park’s Boos and Booze Bar Crawl on October 29th. The tour starts there and then you can visit other bars in the area like Chop Shop and Nick’s Beer Garden. Get tickets here.


Logan Square’s Emporium is hosting a pop-up market called Halloween Hangout on October 29th and 30th. There will be music, movies, a costume contest, and food as well as 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. Every Tuesday and Wednesday in October, they’re hosting a Halloween-themed, double-feature on their rooftop, with the first screening at 5pm and the second at 7:30pm. See the full schedule here.



This October, The Music Box Theatre is hosting a horror movie series called Scared Stupid. Every night, you can expect a wide range of scary movies from classics like Nosferatu to newer cult favorites like Jennifer’s Body. Get tickets and check out the full lineup here.



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 eclectic line-up of movies like Matilda, Night Of The Living Dead, and The Notebook (a true horror movie) can be found here.


Lincoln Park Zoo is hosting a wide variety of events as part of their annual Fall Fest. Throughout October, you can expect installations and pop-ups with things like a harvest maze, professional carvers making jack o'lanterns, and a pumpkin patch. They also have a few scheduled events like "adult's night out" on October 27, with games, a DJ, and cash bar, and Spooky Zoo, a day where kids can show up in costume and trick-or-treat while checking out the animals.


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, during the month of October, they have their Pumpkin Lights. The pier will be decorated with jack o'lanterns and light installations, and will have different festive activities (like axe-throwing and a scavenger hunt) throughout the month. Be sure to check their website for updates.


This October, Replay in Lincoln Park has two TV-themed pop-ups. On the first floor, Stranger Things decorations surround the bar space and arcade games, while the upstairs area features installations based on The Simpsons’ called the Treehouse of Gore. They’ll host events like Simpsons trivia and, if you want to hear what Kate Bush sounds like on violin, they’ll have performances of 80’s hits from Stranger Things by musicians from the Chicago Philharmonic.


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.


photo credit: Nightly Spirits

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Nightly Spirits Ghost Tour Pub Crawl

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 at neighborhood bars along the way. 


Chicago Architecture Center River Cruise

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.

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