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Lloyd the Bartender at Room 237
Photograph: Alexandra Buhrow

The spookiest Halloween events and screenings in Chicago

See an outdoor screening of a classic horror movie, visit a pumpkin patch and enjoy the season at the Halloween events

By Zach Long

You won't be able to parade through Northalsted in your Halloween costume or party all night long in a hotel ballroom during Halloween in Chicago this year, but there are still ways to celebrate the holiday in style. You'll find lots of Halloween events taking place outdoors this October, from screenings of classic horror flicks at Chicago's drive-in movie theaters to a jack-o'-lantern display at the Chicago Botanic Garden. There are even pop-up pumpkin patches within city limits, for those unable to make it out to the burbs to grab a few gourds. Feel free to show off your most creative get-up at these Halloween events and screenings throughout Chicago.

RECOMMENDED: Our complete guide to Halloween in Chicago

Halloween events and screenings

A Nightmare on Elm Street
Photograph: Courtesy Warner Bros

Music Box of Horrors at the Drive-in

Movies Horror Chi-Town Movies Drive-In, Lower West Side

The Music Box of Horrors is usually a 24-hour marathon of frightening, thrilling and chilling movies at the Music Box Theatre, but this year the celebration of scary films will take over a drive-in theater for an entire month. You can expect late-night screenings and double features throughout the entire month of October at the Chi-Town Movies Drive-In, accompanied by specialized intros, pre-show content, filmmaker Q&As vendor and more spooky surprises. The schedule includes mainstream fare like A Nightmare of Elm Street and Carrie alongside more obscure selections like the 1933 Mexican horror flick La Llorona and ‘70s blaxploitation classic Blacula. Check out the complete schedule.

Jack's Pumpkin Pop-up
Photograph: Courtesy Jack's Pumpkin Pop-up

Jack’s Pumpkin Pop-up

Things to do Festivals Jack's Pumpkin Pop-up, River West/West Town

Returning to a 2-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-up saves you a trip to the suburbs by bringing a corn maze, thousands of pumpkins and an array of carnival games to the city. This year's edition of the outdoor event takes a safety-first approach (mandatory timed reservations and masks, no cash transactions, no food and beverages onsite—the list goes on), but you'll still find classic standbys like a full corn maze, fall-themed photo ops and plenty of plump pumpkins. 

JoJo's Pumpkin Patch
Photograph: Courtesy JoJo's Shake Car

JoJo’s Pumpkin Patch

Things to do Quirky events JoJo's Shake Bar, River North

Snag a treat and some decorative gourds at the month-long JoJo's Pumpkin Patch pop-up, an expanded patio adjacent to JoJo's Shake Bar in River North. Groups of six or fewer people can hang out in the 5,000-square-foot space, which is outfitted with hay bales, festive lights and two "pumpkin domes" containing tables. Guests can enjoy a menu of special seasonal dishes, including caramel apples, pumpkin pie, apple pie, spiked ciders and hot chocolate. There's also a decadent Pumpkin Patch Shake, topped with a slice of pumpkin pie, a taffy apple, roasted marshmallow and a Reese's pretzel.

Crypt Run
Photograph: Courtesy Crypt Run

Crypt Run

Sports and fitness Running Various locations throughout Chicago,

Go for a jog in your Halloween costume by signing up for the virtual edition of the Crypt Run, an annual 5K and 10K run or walk that raises money for the Illinois chapter of the Best Buddies program. Participants have all of October to run their own route or follow a provided course through Lincoln Park, which once served as the city's primary cemetery. All crypt runners will receive a T-shirt, face mask and LED spinner light.

Whiskey Business rooftop movies
Photograph: Courtesy Whiskey Business

Whiskey Business Rooftop Movie Night

Movies Whiskey Business, Wicker Park

Don't have a car (or a friend with a car) to park at Chicago's drive-in theaters? You can still catch an outdoor flick at Whiskey Business, which is screening classic Halloween movies on its Wicker Park rooftop every Monday, Tuesday and Thursday in October. The films are projected on two 120-inch screens and everyone in the audience is issued a set of headphones, so you won't have any problem making out your favorite lines. The schedule includes movies like Child's Play, Hocus Pocus and The Craftplus, every ticket includes a bag of popcorn. Check out the Whiskey Business website to snag tickets and take a look at the latest lineup of films. All films screen twice, once at 5:30pm and again at 8:45pm.

Lloyd the Bartender at Room 237
Photograph: Alexandra Buhrow

Room 237

Things to do Morgan Manufacturing, River West/West Town

All work and no play makes Jack (and you) a dull boy—get away from it all for a bit with the help of this The Shining-themed popup, returning to Chicago in a spacious warehouse fit for the social distancing era. Developed by Morgan MFG operations director Amy Teri and Chicago DJ Heaven Malone, this multi-room experience takes guests through a miniature version of the Overlook Hotel, from a giant hedge maze to The Gold Room. Along the way, you'll spot familiar, photo op-friendly props like Jack Torrance's typewriter, the Redrum door and more.

Hocus Pocus pop-up bar
Photograph: Homestead On The Roof/Sarah Zelman

I Put a Spell On You cocktail bar

News Drinking

No Halloween movie marathon is complete without the 1993 family comedy Hocus Pocus, starring Bette Midler, Sarah Jessica Parker and Kathy Najimy as a coven of evil witches vying for immortality. Fans of the flick will want to plan their annual screening around a trip to the new "I Put a Spell On You" pop-up cocktail bar, which opens at Homestead On the Roof on Saturday, October 24. The Hocus Pocus-themed bar will transform the West Town rooftop into a spellbinding experience with a menu to match.

Hideout Chicago, Cosmic Country Showcase
Photograph: Sarah Larson

Cosmic Country Showcase

Music Folk, country and blues Various locations throughout Chicago,

The Hideout's Cosmic Country Showcase celebrates twangy tunes delivered with psychedelic trappings, dressing up the venue's stage to present a wonderfully strange variety show. The streaming Halloween edition of the show features a headlining set from Evil, a banjo-picking singer-songwriter from Virginia who has performed with masked country musician Orville Peck. Other headliners includes Los Espookys writer, performer and star Ana Fabrega, bodily fluid-obsessed comedian Sarah Squirm, local drag artist Nico and yodelin' country singer Nick Shoulders. Stick around to see if Cosmic Country regulars like Andrew Sa, Tenci and Ben LaMar Gay can cast out the evil spirits with the aid of dreamy music and big laughs.

Lauren Elyse
Photograph: Freddie Collier, courtesy of the artist

SCREAMING: A Spooky-Queer Party

Things to do Performances Various locations throughout Chicago,

Join the Museum of Contemporary Art for a spooky-queer Halloween party, streaming directly to your potentially haunted house. Local drag queen Miss Toto hosts the festivities, which include a performance from Fire-Toolz, who specializes in bombastic electronic music that combines elements of vaporwave and heavy metal. Voguer Gravity Balmain and makeup artist Lauren Elyse will be participate in a series of performances and tutorials, while performers and MCA staff help judge a costume contest that any viewer sporting a creative outfit can enter.

Morgan's on Fulton
Photograph: Courtesy Morgan's on Fulton

Moonlit Movie and a Meal

Movies Horror Morgan's on Fulton, West Loop

Morgan's on Fulton and Marvin's Food and Fuel team up for a pair of rooftop movie screenings during Halloween weekend, complete with scares, food and drinks. Attendees can watch Beetlejuice on Friday night or catch Get Out on Saturday night. Each ticket includes access to the movie—once you're seated, you'll be able to order food from Marvin's and some drinks (there is a two drink minimum). The Morgan's on Fulton rooftop is heated and covered, but you'll still need to wear a face covering, so don't forget one!

New Found Glory
Photograph: Acacia Evans

New Found Glory

Music Punk and metal SeatGeek Stadium, Suburbs

The emo-tinged, pop-punk melodies of New Found Glory provide the soundtrack for the first evening of Riot Fest's Halloween Special bash outside of SeatGeek Stadium in Bridgeview. The snotty Florida lifers will likely be celebrating the release of its tenth(!) studio album, which came on the heels of yet another covers album that found the group turning in chugging power chord covers of tracks like "Let It Go" from Frozen and "Eye of the Tiger." After the live performance, stick around to explore the afterlife during a screening of the ’80s classic, Beetlejuice.

arts in the dark 2018, halloween parade
Photograph: Neal O'Bryan

Arts in the Dark Upside Down Halloween Parade

Things to do Festivals Washington Park, Washington Park

Part of Chicago's Halloweek festivities, the annual Arts in the Dark Halloween Parade is happening this year, but it won't be marching down State Street as it has in years past. Instead, registered guests will be able to drive through an "upside down" version of the procession, as dozens of costumed performers and puppeteers line the sides of a street running through Washington Park. Spectators will navigate the route in their car, enjoying the spooky sights along the way.

Presented by the Blommer Chocolate Company (perhaps they'll bring along some of the factory's signature scent), the Arts in the Dark Upside Down Halloween Parade will welcome guests during three hour-long sessions on Saturday, October 31. You'll need to register for the session of your choice via the Arts in the Dark website and show up to drive through the route (it begins in a parking lot just south of the General Richard Jones Armory on Payne Drive) at your chosen time. It's free to attend and you can dress up if you want to!

Knuckle Puck
Photograph: Courtesy Atom Splitter PR

Knuckle Puck + Hot Mulligan

Music Punk and metal SeatGeek Stadium, Suburbs

It's a spooky punk rock party in Bridgeview, as the Riot Fest Halloween Special brings Chicago pop-punk outfit Knuckle Puck to SeatGeek Stadium for a drive-in concert. The local outfit recently released 20/20, a decided uplifting collection of songs that were written well before the world locked down, but provide an antidote to a rather bleak period of history all the same. Michigan alt-rocker Hot Mulligan opens the show, and anyone who sticks around after the music ends will be treated to a screening of The Exorcist. Don't forget to wear your costume and save some room for candy and fair food.

Photograph: Leah Sems

Day of the Deadmau5

Music Dance and electronic SeatGeek Stadium, Suburbs

Mouse-eared EDM mascot Joel Zimmerman (a.k.a. Deadmau5) celebrates Halloween with an outdoor, contactless version of his annual Day of the Deadmau5 shows. Taking up residence at the Chicago Drive-in at SeatGeek Stadium for two consecutive nights at the end of October, Zimmerman will perform "unhooked," ditching his 21-foot-tall cubic DJ booth, but retaining the retina-searing visuals and booming sound production that characterize his live sets. Each ticket for the Day of the Deadmau5 concerts admits a car with four passengers—and don't forget your masks, because you'll be required to wear one outside of your vehicle.

Visit one of Chicago's most haunted places

Holy Name Cathedral
Photograph: Andrew Nawrocki

The 16 most haunted places in Chicago

Things to do

If none of these Halloween events are scary enough for you, why not celebrate the spooky holiday by going where the ghosts are? We've gathered 16 haunted places throughout the city and some advice from local paranormal researchers for anyone hoping to have an encounter with otherworldly spirits this October.


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