SPOOKY, BUT MAKE IT A WHOLE ITINERARY
I LOVE haunted houses. Like, willingly paying money for someone to chase me through a dark room? Sign me up. But I know that is very much not everyone’s cup of tea, so I promise this list isn’t just things that’ll make you scream.
I rounded up everything from creepy nights out and costume parties to pumpkin-filled plans, free events, family-friendly stuff, and plenty of ways to do Halloween without sleeping with the lights on.
oh my gourd!
Photo via Chicago Botanic Garden
Oct. 7–11, 14–18 & 21–25
6:30–10:30 PM
Chicago Botanic Garden
I’m a sucker for anything that makes me feel like I fully stepped into Halloween, and this is exactly that. Thousands of hand-carved pumpkins glowing through the Botanic Garden at night? I’m bundling up, grabbing something warm to drink, and taking approximately 400 pictures.
Photo via Jack’s Pumpkin Pop-Up
Sept. 19–Nov. 1
Mon–Thu: 5–10 PM
Fri: 4–11 PM
Sat: 12–11 PM
Sun: 12–10 PM
1265 W. Le Moyne St., Chicago, IL
If I’m doing a pumpkin patch, I want the whole production. Jack’s has pumpkins, a corn maze, games, drinks, and enough fall photo ops to absolutely destroy my camera roll. It’s basically one giant excuse to lean way too hard into fall.
Photo via Arts in the Dark
Oct. 24
6–8 PM
Columbus Drive in Grant Park
331 E. Randolph St.
There’s something about a giant nighttime parade in October that just feels right. The costumes, massive puppets, performers, and absolute chaos rolling through downtown make this one of those Halloween traditions I’d happily stand on the sidewalk for every year.
FREE HALLOWEEN PLANS
Photo via Lincoln Park Zoo
Oct. 17
10 AM–1 PM
Lincoln Park Zoo
I know not everyone wants their Halloween plans to involve being chased with a chainsaw, so this one’s for the cute-spooky crowd. Costumes, trick-or-treating, animals, and a free day at Lincoln Park Zoo? Honestly, an adorable little Saturday.
Photo via Northalsted
Oct. 31
7–8 PM
Halsted St. between Aldine Ave. and Addison Ave.
If you’ve been saving your Halloween costume for one big night, this is where I’d wear it. Halsted goes completely off with wild costumes, a parade, performances, and a whole neighborhood ready to party. People really show OUT for this one.
Throughout October
Times vary by event
Multiple Chicago Park District locations
Sometimes I just want a cute neighborhood Halloween moment without turning it into a whole expensive production. Chicago parks have pumpkin patches, haunted houses, movies, parties, trick-or-treating, and random spooky little events all month, so there’s probably something happening close to you.
Spirits with spirits
Photo via Lincoln Park Zoo
Oct. 23–24
6:30–10 PM
Lincoln Park Zoo
Drinking craft beer at the zoo after dark while everyone’s dressed for Halloween feels slightly unhinged, which is exactly why I’m into it. Add cider, costumes, and Lincoln Park Zoo at night and suddenly my regular beer tasting has gotten way more interesting.
Photo via I|O Godfrey
Oct. 31
8 PM–2:30 AM
I|O Godfrey Roofscape Chicago
A rooftop Halloween party is already enough to get me there, but I|O Godfrey turning into a full-on spooky camp situation? Yeah, I’m listening. Get dressed up, grab a drink, and prepare to stay out much later than you originally promised yourself.
Photo via Boos & Booze Halloween Bar Crawl
Oct. 31
The Butcher’s Tap
Headquarters Beercade
PB&J: Pizza Beer and Jukebox
If your Halloween tradition is basically putting on a costume and seeing where the night takes you, this has your name all over it. A bunch of River North bars, people fully committed to the bit, and zero chance you’re making it an early night.
FOR THE certified scream queens
Oct. 24
8 PM–12 AM
Colvin House
This feels like the pick for anyone who wants Halloween to get a little weird. Colvin House already has the perfect moody setting, and filling it with immersive performances and eerie surprises sounds exactly like the kind of night I’ll be talking about afterward.
Photo via Empty Bottle
Oct. 25
9 PM
Empty Bottle
Ukrainian Village
I love a Halloween plan that isn’t the usual haunted house or bar crawl. A weird, theatrical Dracula show at Empty Bottle feels perfectly offbeat, a little campy, and very much for the people who want their spooky season with some personality.
Photo via Chicago’s First Lady Cruises
Daily through Nov. 1
Select times
Chicago’s First Lady Cruises
112 E. Wacker Dr.
I’ve done the architecture cruise thing, but putting me on the Chicago River after dark with spooky stories and Halloween energy is a completely different vibe. This feels perfect if you want something creepy without signing yourself up to be actively terrorized.
FAMILY FRIENDLY SPOOKY SEASON
Photo via Brookfield Zoo Chicago
Oct. 3–25
Mon–Fri: 10 AM–5 PM
Sat–Sun: 10 AM–6 PM
Brookfield Zoo Chicago
Brookfield Zoo in October is already an easy sell for me, but throw Halloween into the mix and I’m there. Costumes, seasonal activities, animals, and enough spooky touches to feel festive without traumatizing anybody? Very solid daytime Halloween behavior.
Photo via Chicago Park District
Oct. 24
10 AM–2 PM
Dvorak (Anton) Park
Not every fall plan needs to involve driving an hour outside the city. I love that you can get your pumpkin patch fix right in the neighborhood, make a whole little fall morning out of it, and still be home before the Sunday scaries kick in.
Updated October 2026
Did we miss your favorite spooky season event?
Let us know, and we’ll add it to the list!
