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Chicago has a complicated past and an impressive collection of ghosts. Former cemeteries, notorious gangsters, haunted hotels, and enough unsolved mysteries to keep the city’s ghost tour operators busy all year.
And when Halloween comes around, Chicago really gets into it. People spend weeks decorating their houses, costumes become serious business, and entire neighborhoods turn out for parades that put most Halloween parties to shame.
But what I find most interesting about Halloween in Chicago is how much of the spooky stuff is rooted in real history. You can visit the site of one of America’s deadliest theater fires, explore a former cemetery beneath a zoo, or spend the night in a hotel with a century’s worth of ghost stories.
Here are my picks for Halloween in Chicago in 2026, from the big celebrations to some wonderfully strange experiences you might otherwise miss.
Best Things to Do for Halloween in Chicago 2026
Chicago has no shortage of Halloween entertainment, but in 2026, I’d make room for the city’s famously extravagant parades, a 24-hour horror movie marathon, a haunted house populated by puppets, and a few other unique ways to celebrate.
Watch giant puppets take over downtown at Arts in the Dark
Of all Chicago’s Halloween traditions, Arts in the Dark might be the most visually spectacular.
It’s a parade, but not the sort with politicians waving from convertibles and marching bands playing the same three tunes.
Organized by LUMA8, it brings together artists, dancers, musicians, puppeteers, and cultural organizations from across Chicago. There are enormous illuminated puppets, elaborate costumes, circus performers, and floats that look like they’ve escaped from someone’s imaginative dream.
The parade returns to Columbus Drive in 2026. With the downtown skyline as a backdrop, it should be quite a sight. And it’s free and open to everyone. The organizers recommend the southern end of the route for anyone hoping to avoid the biggest crowds.
- When: October 24, 6–8 PM
- Where: Columbus Drive, from Balbo Drive to Jackson Boulevard
- Admission: Free
See Chicago’s wildest costumes at Haunted Halsted
If you happen to be in Chicago on October 31, make room for Haunted Halsted.
The annual parade through Northalsted, the city’s historic LGBTQ+ entertainment district, is celebrating its 30th anniversary in 2026. Over the years, it’s earned a reputation for spectacular costumes, drag performances, and a very enthusiastic crowd.
The costume competition is a big part of the attraction. Some participants spend months planning their outfits, and the results can be impressively elaborate. You can come dressed up or simply watch from the sidelines, although I’d imagine the temptation to join in is considerable.
This year, the celebration expands into a five-block daytime festival before the evening parade, so there’s more to do than just turn up for the procession.
- When: Saturday, October 31, 2026; evening parade at 7 PM
- Where: North Halsted Street, Northalsted
- Tickets: Free to watch
Enter a haunted house made entirely of puppets
House of the Exquisite Corpse is Chicago’s puppet haunted house, now in its sixth Halloween season. Six teams of local artists create separate horror environments, each with its own disturbing characters and atmosphere.
The theme for 2026 is lullabies, and we all know how easily childhood songs, bedtime stories, and dolls can become the stuff of nightmares.
The combination of puppetry, theatrical design, and horror makes it one of the more original Halloween events I’ve come across.
- When: October 8 – November 1
- Where: Steppenwolf Theatre
- Admission: Ticketed
Spend 24 hours watching horror movies
Every October, Chicago’s historic Music Box Theatre gives horror fans a good reason to lose an entire night’s sleep. Music Box of Horrors is a 24-hour movie marathon featuring cult classics, rare screenings, obscure horror films, and special guests.
The 2026 edition kicks off with Buster Keaton’s 1921 silent comedy The Haunted House, accompanied by live music. From there, the program takes a darker turn, with films running continuously until noon the following day.
You don’t have to commit to all 24 hours, but for dedicated horror fans, I guess that’s the point. And, thinking about it, there are worse places to spend a sleepless night than a beautiful 1929 movie theater.
- When: October 24, starting at noon
- Where: Music Box Theatre, 3733 N. Southport Avenue
- Admission: Ticketed
Admire some impressive pumpkin carving
There’s pumpkin carving, and then there’s what happens at the Chicago Botanic Garden, where ordinary jack-o’-lanterns become elaborate works of art.
For Night of 1,000 Jack-o’-Lanterns, professional artists carve astonishingly detailed designs into hundreds of pumpkins, including 75 giants weighing around 150 pounds each. Visitors follow an illuminated trail through the gardens, with live carving demonstrations and costumed performers along the way.
It’s outside Chicago proper, in Glencoe, but I’d consider making the trip.
- When: October 7 – 11, 14 – 18, and 21 – 25, 6:30 – 10:30 PM
- Where: Chicago Botanic Garden, Glencoe
- Admission: Ticketed
Do the Time Warp at the Chicago Theatre
The cult classic The Rocky Horror Picture Show is coming to the Chicago Theatre for a special screening of its newly restored 4K version, with appearances by members of the original cast.
First released in 1975, the film has developed one of cinema’s most devoted followings, with audiences famously dressing as characters, shouting back at the screen, and joining in with the songs. It’s a movie that’s become as much about the audience as what’s happening on screen.
And if you’ve never been inside the Chicago Theatre, the venue alone is worth seeing.
- When: October 31
- Where: Chicago Theatre, 175 N. State Street
- Admission: Ticketed
Take the kids to an upside-down Halloween parade
Instead of having children stand around waiting for a parade to pass, let them become the parade.
At Chicago’s Upside Down Halloween Parade, families walk along a route lined with performers, dancers, musicians, acrobats, and costumed characters. The entertainment stays in place while the audience moves.
Organized by the same team behind Arts in the Dark, it’s a free daytime celebration designed especially for families. Every child receives a bag of Halloween treats at the end. I like the concept. After all, why should the grown-ups have all the fun dressing up?
- When: October 31, noon–2 PM
- Where: Washington Park
- Admission: Free
Chicago’s Haunted Places and Ghost Tours
Chicago has plenty of material for a good ghost story. The Great Fire of 1871, the city’s violent gangster era, disastrous theater fires, and old buildings with colorful histories have all contributed to its supernatural reputation.
Whether you believe in ghosts or not, some of these stories are worth investigating. And October is the best time to do it, with special after-dark tours that explore the city’s unsettling history.
Explore the cemetery beneath Lincoln Park Zoo
In the 19th century, before Lincoln Park became the pleasant lakeside green space it is today, the land was used for burials. Many graves were relocated as the city expanded, but not all of them. In 1998, construction workers uncovered the remains of more than 80 people, including a nineteenth-century iron coffin.
So, yes, the zoo has an unusual history.
Throughout October, Chicago historian and author Adam Selzer leads after-dark walking tours exploring the cemetery’s past and the ghost stories that have accumulated over the years.
I’d choose this over a conventional haunted house any day. The history is strange enough without anyone jumping out from behind a tree.
- When: Tuesdays and Wednesdays through October 28, 2026; 7 PM and selected 8:30 PM departures
- Where: Lincoln Park Zoo
- Tickets: $35 for nonmembers; ages 16+
Discover the darker side of Chicago’s industrial past in Pullman
Pullman is one of Chicago’s most fascinating neighborhoods, and a place many visitors never think to explore.
Built in the 1880s as a planned industrial community for workers manufacturing Pullman railroad cars, it was supposed to be a model town. Beautiful brick houses, landscaped streets, and amenities provided by the company. Of course, life in a company town came with its own complications.
The Macabre Pullman Tour takes visitors through this historic neighborhood after dark, concentrating on some of its less cheerful stories: train crashes, murders, mysterious deaths, and the alarming state of 19th-century medicine.
It’s a clever premise for a Halloween tour, particularly because the neighborhood itself is so interesting. You get an introduction to Chicago’s industrial history along with the gruesome details.
- When: October 22 and 30, and November 5, 2026
- Where: Pullman neighborhood, South Side
- Tickets: Paid guided tour; advance booking recommended
Hear about the Devil Baby at Hull-House
A Devil Baby, a Lady in White, and a neighborhood mortician sound like characters from a strange Gothic novel. But they’re actually part of the folklore surrounding Jane Addams Hull-House.
Founded in 1889, Hull-House became one of America’s most influential social settlements, providing education, social services, and a meeting place for Chicago’s immigrant communities. But alongside its serious work, the building acquired an extraordinary collection of supernatural stories.
The most famous concerns the Devil Baby, a supposedly horned infant with a tail and cloven hooves. The story spread through Chicago in the early 20th century, drawing curious visitors to Hull-House. Jane Addams herself wrote about the legend and what it revealed about the lives of the women who told it.
The museum’s Halloween folklore tours explore these stories in the context of the neighborhood’s immigrant history.
- When: Thursdays and Fridays, October 8 – 23, 2026, 6 – 8 PM
- Where: Jane Addams Hull-House Museum, 800 S. Halsted Street
- Tickets: Paid guided tour
Hunt for ghosts along Chicago’s Millionaires’ Row
Prairie Avenue was once one of Chicago’s most prestigious addresses, home to wealthy industrialists, including Marshall Field and George Pullman. But behind the grand mansions and elegant facades, there are plenty of unsettling stories.
The Prairie Avenue Haunted History Tour and Ghost Hunt takes you through this historic neighborhood, past surviving Gilded Age mansions, churches, and landmarks. Along the way, you’ll hear tales of the area’s former residents and try your hand at ghost hunting with EMF meters, dowsing rods, and spirit boxes.
It’s an unusual way to explore one of Chicago’s most interesting historic districts. And even if you don’t manage to make contact with the other side, the architecture alone makes the walk worthwhile.
- When: Check available dates
- Where: Prairie Avenue Historic District, Chicago
- Tickets: Paid guided tour
Where to Stay for a Haunted Halloween
If you’re going to spend Halloween in Chicago, you might as well consider a hotel with a ghost or two. The city has several historic properties with supernatural reputations, although some have more convincing stories than others.
Congress Plaza Hotel
Built in 1893 to accommodate visitors to the World’s Columbian Exposition, the Congress Plaza Hotel has collected enough ghost stories to fill a book.
There’s Peg Leg Johnny, a mischievous spirit said to haunt the South Tower, a ghostly little boy on the 12th floor, and the mysterious woman in Room 441, where guests have reported moving objects, flickering lights, and being disturbed in their sleep.
Al Capone is also rumored to have frequented the hotel, although some of the stories connecting him to the property are questionable.
Whether any of this is true is another matter, but if you’re looking for a hotel with a spooky reputation, this is probably Chicago’s most famous.
The Drake Hotel
For something a little more glamorous, there’s The Drake, a Chicago landmark that opened on New Year’s Eve in 1920.
Its best-known ghost is the Woman in Red, supposedly a young woman who discovered her fiancé with another woman at the hotel’s opening-night celebration and jumped to her death. According to the legend, she still wanders the halls and occasionally appears in the Gold Coast Room.
Whether the Woman in Red ever existed is anyone’s guess, but The Drake has plenty of real-life charm. Its grand Palm Court, elegant 1920s interiors, and prime location on the Magnificent Mile make it a tempting place to stay, ghosts or no ghosts.
How Chicago Celebrates Halloween
One thing Chicago does particularly well at Halloween is decorating its houses. And some residents go to extraordinary lengths. We’re talking entire front yards turned into graveyards, skeletons climbing up Victorian facades, enormous spiders dangling from balconies, and enough artificial cobwebs to wrap a small building.
Lincoln Park, Lakeview, and Old Town are particularly good neighborhoods for an October stroll, with their historic houses and tree-lined residential streets. Some displays are impressively elaborate, and it’s worth wandering off the main roads to see what people have come up with.
On Halloween itself, residential neighborhoods fill with children going door to door for candy, often starting before sunset. Meanwhile, adults head to costume parties, bars, and neighborhood celebrations, with Northalsted hosting some of the city’s most extravagant outfits.
Chicago Weather in October and What to Wear
Chicago in late October can be beautiful, with golden autumn leaves, crisp sunshine, and temperatures that make walking around the city a pleasure. It can also be cold, windy, and thoroughly miserable, sometimes all in the same day.
Around Halloween, daytime temperatures typically hover around 50 – 55°F (10 – 13°C), dropping to approximately 40°F (4 – 5°C) at night. Rain is always a possibility, and the wind off Lake Michigan can make it feel much colder than it is.
Pack layers, a warm jacket, and comfortable shoes that can handle a little rain. Gloves and a scarf aren’t a bad idea either, especially if you’re planning to spend the evening outdoors.
As for Halloween costumes, I’d think twice before going as a scantily clad vampire or anything involving bare legs. Chicago’s weather has absolutely no respect for your creative vision.
The Origins of Halloween in Chicago
Halloween arrived in Chicago with the waves of Irish and Scottish immigrants who settled in the city during the 19th century, bringing traditions associated with the ancient Celtic festival of Samhain and the Christian observance of All Hallows’ Eve.
Early celebrations looked quite different from today’s. There were parties, fortune-telling games, apple bobbing, and the occasional prank. By the early 20th century, Halloween mischief had become something of a problem in American cities, with youngsters overturning garbage cans, soaping windows, and causing real trouble.
Organized community celebrations and supervised activities gradually helped turn Halloween into a more family-friendly holiday. Trick-or-treating became widespread in the mid-20th century, and costumes, candy, and elaborate decorations eventually became part of the annual ritual.
Chicago has since made Halloween its own, adding neighborhood parades, artistic performances, and some spectacularly ambitious costume competitions to the traditions brought over generations ago.
Practical Tips for Halloween Weekend in Chicago
Don’t plan two parades on opposite sides of town. Arts in the Dark takes place downtown on October 24, while Haunted Halsted is in Northalsted on October 31. They’re a week apart, so check your dates before building an itinerary around both.
Take the ‘L’ to Northalsted. The Red Line’s Addison and Belmont stations are convenient for the Halloween celebrations. Driving into the neighborhood on parade night is asking for trouble, especially with street closures.
Book ghost tours before you arrive. Lincoln Park Zoo’s Haunted History Tours and the smaller museum-led walks have limited places. The same goes for unusual theatrical events, where there may only be a handful of performances.
Don’t underestimate the distances. Pullman is on the Far South Side, while the Chicago Botanic Garden is in suburban Glencoe, roughly 25 miles north of downtown. Neither is something you casually squeeze in between two Loop attractions.
Explore the residential streets. Lincoln Park, Lakeview, and Old Town are good places to admire Halloween decorations. Wander around the side streets, especially near the historic houses, where residents sometimes go spectacularly overboard.
Remember that Halloween falls on a Saturday in 2026. Expect busy bars, crowded trains, and plenty of costumes on the evening of October 31. If you’re planning dinner before a party or parade, reserve a table.
Keep an eye on the CTA’s service alerts. Chicago’s trains are useful for getting around, but weekend maintenance and temporary station changes happen. Check CTA service alerts before setting off, particularly if you’re heading somewhere unfamiliar.