Things To Do

30 Terrifyingly Fun Things To Do This Halloween In Chicago

By Colby Smith

30 Terrifyingly Fun Things To Do This Halloween In Chicago

Halloween isn’t dead… or is it?

It’s safe to say that 2020 has already struck a tone of fear our lives. Horror movies, haunted houses, and fake-blood-soaked events are thus a refreshing dose of staged, not-existential fear that’s all the more welcome this year. While the spooky holiday is a little stranger this year, there’s still at least 13 frighteningly fun things you can do this Halloween season!

1. Go Down The Rabbit Hole For The Mad Hatter’s (Gin &) Tea Party

The Mad Hatter is bringing his infamous gin and tea parties to Chicago! In this immersive, theatrical cocktail experience you’ll enjoy a menu of delicious Rabbit Hole Bespoke Gin concoctions in the most psychedelic of settings. Costumes are welcome, but if you don’t have time to put an outfit together don’t worry— the Hatter will be lending out some of his craziest hat creations! Want a seat at the tea party table? Get your tickets here! ⭐️Sponsored⭐️

2. Pop In To A Horror Pop-Up

While 6th Dimension Space’s Horror Museum could simply rig a TV set in the middle of an empty room tuned into any given news outlet to instill fear, the space is taking the extra step to scare your pants off in mid October. The two-story exhibition will feature countless real-world stories taken straight out of Stephen King’s worst nightmares: demonic possessions, paranormal encounters, witchcraft, and tales of folklore.

3. Dine In Pitch Darkness

Imagine. You’re seated at a table in a room shrouded in darkness. You tremulously reach for your glass. It’s all too eerie, but the first of three courses has just been served — seemingly out of thin air — and already your senses are reeling. There’s an air of ominousness, but your taste buds have never been this heightened before, and with food this tantalizing, you can’t leave. This is the Haunted Dining in the Dark experience.

4. Lurk In The Light Of 1,000 Jack-O-Lanterns

This year, the Chicago Botanic Garden is going full Tim Burton with their Halloween event, Night of 1,000 Jack-O-Lanternsfor 10 spooky nights starting October 14! Even though you won’t be able to eat any of the pumpkins on display at Chicago Botanic Garden’s Night of 1,000 Jack O’Lanterns, you can still admire the brilliant intricateness of the many many hand-carved pumpkins — with some weighing up to 150 pounds!

5-7. Scream Your Head Off At A Drive-In Movie

Fright Night brought to you by PR Pop Ups is a one-of-a-kind Halloween experience! This drive-in experience includes costumes, candy, food trucks, a bar and a double feature drive-in movie. Parking spots are first come – first serve, doors open at 7pm for the first movie. You will have your own private socially-distant parking spot to enjoy the event. You may sit in a lawn chair outside, in front of your vehicle. You may also sit in the bed of your truck or in the back of your vehicle with your hatch open. A Pop-Up Drive-In allows you to be able to safely practice social distancing and still enjoy a sense of community. Bring the whole family, bring your mask, and enjoy the experience.

  • Join the crew at PR Pop Ups at the all-new Cross Pointe Park come out and enjoy the nostalgia of a Drive-In Movie close to home. Bring the whole family, bring your mask, and enjoy the experience. There will be a food truck and bar on-site. However, you can bring your favorite food/snack and non-alcoholic beverages from one of the towns great local restaurants. Have your own private, socially distant spot to enjoy the movies. You may sit in a lawn chair outside, in the front of your vehicle.
  • It’s official: 2020 is cursed. But Chicago’s 90-year-old independent cinema, Music Box Theatre, is making the most of it with a treat for horror fanatics. Throughout the entirety of October, the theatre will be overtaking the Chi-Town Movies Drive-In with a 31 Nights of Terror drive-in series!

8. Slay The Competition At Old Ground Social’s Drag Bingo Night

Have the past few months been a little less-than-dazzling? We feel that. To put a little sparkle back into our lives, the queens over at Old Grounds Social are hosting Drag Bingo on Thursdays with dancers, prizes, drink deals including $20 domestic beer buckets, $25 champagne buckets, and shot specials throughout the night for a fabulously fun time!

9. Freak Out Your Friend

Scare Your Friend is a bundling of two of Psycho Clan’s wildly popular blindfolded haunted houses – The Empty Place and A Dark House. Now, they are available to the public as audio downloads that come with digital how-to manuals that guide you in staging these unique horror experiences safely in the privacy of your own home! Your personal surroundings and your own imagination will bring the whole experience alive. Both shows can be done at home and should be done either with one other person or with small groups of people who you live with or with whom you have formed social cohorts. You can share the download up to 20 times! If you are tired of participating virtual experiences on a screen, this is safe…but will raise the hair on the back of the neck. This is a Halloween treat (or beyond) that gets you up and on your feet!

10. Walk With Ghosts

They wrote the book(s) on Chicago ghosts! Now they are in their 18th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago’s haunted history over more than two decades. Chicago Hauntings is the original Chicago ghost tour and still the best. These tours are based on all original research, unlike the many other knock-off tours you’ll find today. Beware of the imitations. Imagine walking in the steps of Chicago’s most notorious criminals at the city’s original courthouse, putting your fingers into actual bullet holes from Chicago’s gangland days, feeling the haunting presences near the site of the old Cook County gallows, and gazing upon the waters where 844 souls lost their lives in the horrific Eastland disaster of 1915. Come along and experience all this and more!

11. Howl At The Moon

While plans on the ground have taken a scary turn and most major Halloween events have been canceled, nature will be stepping in to put on a spooky show of its own. If you’ve ever wondered how the saying “once in a blue moon” came about, it was coined from the unique celestial phenomenon where we get two full moons in one calendar month or the third of four full moons in a season. The second full moon in a month (or third of the season) is called a Blue Moon. This happens every two to three years and the next one is happening on October 31, 2020.

 12. Shoot Zombies With Lasers

Photo credit: @theforgelemont

The Forge: Lemont Quarries just outside of Chicago is loaded top-down with action-packed entertainment for anyone and everyone to enjoy. With Halloween around the corner, the park has unleashed a Zombie Apocalypse laser tag game that’s out of this world. Don’t take from us though, get word straight from the source:

“Adventure comes in endless forms at The Forge: Lemont Quarries and our tactical laser tag arena is the perfect example,” the park writes on their website.  “Playing tactical laser tag is a great way for people age 8 and up to experience the thrill of simulated combat experience without the pain and added expense of paintball.  Experience hyper-realistic sound effects while playing with military-grade replica weapons in small teams or large groups.”

13. Pull Into A Drive-Thru Haunted House

If you heeded your parents’ advice as a child to never wander into dark alleys, then buckle your seatbelt because this drive-thru haunted house experience is about to take you for a ride! On October 2, Replay in Lincoln Park will debut its drive-in haunt, Alley of Darkness:

“Our haunt is set in an alley in the shadows of the Red Line where a horrible incident occurred not long ago,” Replay has written on the event. “You’ll first settle in with a drive in movie experience that sets the narrative. The undead, demons, zombies and more jump out at and rock your car accompanied by sound effects and sprays of blood. That’s right… your car gets covered in blood.”

14-15. Bring Your Painting Skills To Life

The 1.5 hour course is led by an expert artist to guide you through the creation of a painting inspired by the Dias de Muertos. Release your creativity while painting along. No experience needed! List of recommended supplies: a canvas or canvas board, a big brush, a skinny brush, a water cup, paper towel, a plate, a pencil and an eraser, paint (blue, yellow, red, black, and white), and an apron or painting clothes.

  • This class is a Halloween virtual painting party! This 1.5 hour course is led by an expert artist to guide you through the creation of a spooky painting inspired by Halloween. Release your creativity while painting along. No experience needed. List of recommended supplies: a canvas or canvas board, a big brush, a skinny brush, a water cup, paper towel, a plate, a pencil and an eraser, paint (blue, yellow, red, black, and white), and an apron or painting clothes.

16. Pick Out A Pumpkin

Is there anything more representative of the fall season (outside leaves) than the pumpkin? Whether it’s sipping on a pumpkin spice late, digging into pumpkin pie, or re-reading instructions on how to properly carve a jack-o-lantern, the pumpkin is (literally, in the latter case) the face of autumn. Eat it, carve it, or smash it, get your hands on one of your own at one of these bountiful pumpkin patches around the Windy City.

17. Roam The City For Lost Spirits

Chicago is an enchanting city, perhaps, more enchanting then you might hope. With a complicated history rife with tragedy, the city’s spiritual underbelly finds a way to show its ghostly face to unsuspecting witnesses. Meet the local ghosts in your neighborhood with this list of the 10 most haunted places in Chicago.

18. Walk Into A Haunted House

Remember when haunted houses were simply makeshift stages at your neighbor’s? Some of the parents would string up a few cotton cobwebs, black curtains, and maybe one of the dads would dress up as a vampire and do that one laugh? Well those days are long and gone. Not only is the world itself a more terrifying place to be, but haunted houses have gone to hell and back to scare the absolute bejesus out of you.


19. Check Out The Changing Leaves

If you can’t get enough of the fall foliage, or just feel like doing a cannon ball into a big ole pile of crackling leaves, follow the link to discover our favorite places to watch the changing of the seasons in Chicago.

20. Escape Into The VR World Of Lovecraft

Sanctum Haunted VR Escape Room: The world of H.P. Lovecraft is full of dark places and mystical creatures that you should stay away from. You received a letter from your close friend Anna, a detective conducting an investigation of mysterious disappearances in the nearby forests. Now you have no other choice but to do everything to save her…House Of Fear Escape Room takes place in the dead of night. An abandoned dilapidated cabin in the woods. Cobwebs in the corners, dust on the floor, dilapidated furniture and… not a single living soul. From the looks of it the house has long since been abandoned, but is that really the case? What better way to celebrate the spooky season than with one of these VR escape rooms with your friends?!

21. Sip On Some Spiked Cider

Photo credit: @caferobey

There are two top contenders vying for the title of the true fall drink: the pumpkin spice latte and hard apple cider. While the former has pumpkin (big plus) and caffeine, the latter has alcohol — a slight advantage, we’d say. Get your fill of all the warm fuzzy feelings of fall by visiting one of these watering holes for a cup of spiked apple cider.

22. Meet The Pumpkin Dinosaur

If you’re like one of us and whole-heartedly embrace everything autumn, you’ll want to take a short trip down to Goebbert’s Pumpkin Patch, where they’ve got tons of seasonal attractions for the whole family, including a pumpkin-eating dinosaur!

23. Go On A Haunted Pub Crawl

Bad news, Chicago, evidently we’re one of the most haunted cities in America. Bars, buildings, parking lots, theaters — all possessed by undead spirits dating back to the 1800s. Nightly Spirits gives you the opportunity to meet your incorporeal neighbors while unmasking the freaky history that plagues the local neighborhood. But keep your spirits up, the tour also makes a number of boozy stops at local haunts along the way.

24. Dine With Dracula

One hundred years after Dracula’s demise, the descendants of his destroyers reunite to commemorate the event. But plans change when one of the partygoers exhibits signs of turning into a vampire! Who is transitioning from life to undeath, and which room of the castle holds the solution? During this Virtual Murder Mystery Clue Chase, a dinner party that takes place in real-time, you’ll play a character and work together with your fellow dinner guests to find the vampire and either help them regain humanity or seal their fate… all before dessert!

25. Pop Into A Pumpkin Pop-Up

Fall has officially landed in Chicago and with it, Jack’s Pumpkin Pop-Up. This celebration of fall is one of Chicago’s most popular Halloween-time events. It’s also the only one that takes place 100% outside. Last year there was a hidden bar for you to reward yourself with a hard cider or Tito’s cocktail after making it through the corn maze! While the pop-up has yet to release its official opening dates, Jack’s has announced its official return on social media.

26. Lift Your Spirits At Lincoln Park’s Zoo

Be sure to mark your calendars for Adults Night Out: The Great Pumpkin Glow at the Lincoln Park Zoo, October 29, where adults can (trick or) treat themselves to a hauntingly good time:

“Enjoy seasonal activities—such as a corn maze, a pumpkin walk, a haunted trail, themed food, and seasonal cocktails—at this unique after-hours experience. No kids. No crowds. Just strolling among exhibits with a beer or hot cider in hand. Sound fun? Join us!”

27. Try Your Hand At Streetart In This Halloween BYOB Urban Art Workshop + Costume Party

Let your inner creative child out in more ways than one this Halloween. Dress up in costume and head down to The Chicago Kedzie Plaza to try your hand at some urban art. The weekly workshop is now running a Halloween themed event and you’re invited to bring your own booze down to enjoy the fun. You will help bring to life an original horror-themed design created by one of our Native 312 Artists. Materials, a mini canvas, and fumeless VOC spray paint are included with every ticket and some of the best street artists are on hand to guide you.

This interactive workshop allows you to grab some spray paint and design your own mural while collaborating with other guests and learning about the essential elements of Urban Art. Each participant takes home a custom print of the artist’s original concept and the winner for best costume will take home a prize at the end of the night.


28. Test Your Patience At The Midnight Terror Haunted House Daytime Tour

Ranked one of the best haunts in the nation by USA Today and voted Illinois #1 Must-See Haunted House, Midnight Terror’s expansive playground spans over 26,000 square feet and more rooms than we can count. Need we say more?

Every Saturday and Sunday of October theatrics, special effects, twists, and tight turns await you in the “Factory of Malum,” and “Black Oak Grove.” This Night of Fear won’t finish when you think, you’re in for surprises throughout the evening. The Daytime Scenic tour includes all the magical special effects of the regular event but removes the actors to limit as much person to person interaction as possible in the current circumstances.

29. See How Safe You Feel On  Four Wheels With The Highway of Horror Haunted Halloween Drive-In Experience

Every Thursday through to Sunday from October 15th until the beginning of November brave souls will be trying their best to stay calm in a derelict lot in the shadows of Chicago’s iconic Loop. Nestled against the highway 90/94 where horrible incidents occurred in the recent past sits a drive-in experience that’ll have you quaking in your car. Demons, zombies, and hordes of the undead lie in wait, ready to pounce. Expect your car to be rocked, sprayed with blood, and convincing sound effects make the hairs on the back of your neck stand on end. This is a drive-in haunted house where you’ll spend one hour and a half confined to your car waiting for the horror to end. Courageous enough but carless? Not an issue – private geodesic domes are rented out to and aired and sanitized between haunts. Get ready for fear to you from all directions.


30. The Dime Dynasty Halloween Drag Brunch

The Dime’s 2nd official drag brunch makes for a Halloween morning to remember and the marvelous Mahogany Charlotte is a host you certainly won’t forget! A fabulous show is accompanied by bottomless mimosas and bloody marys with a complimentary entrée. Food can be purchased at the restaurant if desired but above all, expect creepy and convincing costumes in every corner! So dig out your best outfit as the winner of the costume contest will receive a complimentary brunch for four people at a later date.


See also: 59 Freakin’ Awesome Things To Do In Chicago This October