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25 Terrifyingly Fun Things To Do This Halloween In Chicago

Elliot McGowan Elliot McGowan

25 Terrifyingly Fun Things To Do This Halloween In Chicago

Ghouls just wanna have fun.

It’s safe to say that the last year or so struck a tone of fear in 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.

The witching hour is close at hand, soon the ghosts will come out to play, cackling witches will soar into the skies and ghoulish creatures will creep out from their lairs. Halloween is almost upon us and we’ve already started planning for the spookiest nights of them all.

From ominous candlelit concerts to blood-curdling haunted prisons, here are 20 of the best plans and events taking place in Chicago to help you creep it real this Halloween.

1. Book into the Sleepy Hollow Bar: Immersive Cocktail Experience

Sleepy Hollow Bar: An Immersive Cocktail Experience is taking place now through Halloween and your presence is requested in the Western Woods where they say no sane person should go!

You will find a clearing under the moonlit sky: a spot hidden in the woods overflowing with cocktails, dark music, merriment, and life! As our opening-night guest, we welcome you to enter our tavern and enjoy three gothic drinks. We fine folk may have a gift for you here, as well as Godforsaken games of yore to enjoy at your leisure… perhaps you may even experience the rare touch of the undead.

You may have heard the Hollow is a place where blood runs cold, haunted by a warrior without a head and bathed in red. But please, worry for naught! What awaits you is an eve of fantastical joy, in woodlands that are yours to explore!

Get your tickets here.

2. Be captivated by a Halloween Candlelight Concert

Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but it is in the crisp air of autumn when the concerts reach their peak and this Halloween some extra-special concerts are taking place.

This October, let the ominous yet melodic sounds possess you for a Haunted Evening of Classic Compositions at Chicago’s iconic Salvage One venue.

See the full list of candlelight concerts taking place in Chicago here.

3. Party hard at RADIUS

Come on down to Chicago’s brand new state-of-the-art concert venue RADIUS for an unforgettable Halloween party on Saturday 30th! This night will be full of talent, with world-class DJ Alan Walker headlining the night with support from KREAM. Get ready to party the night away, and don’t forget to dress to impress in your spookiest costumes and be in with the chance of winning a cash prize of $2500! Get a ghoulish group of friends together and get your tickets now!

Get your tickets here.

4. Head to Jack’s Pumpkin Pop-up

With fall’s arrival come a plethora of pumpkin patches. Our pick of the bunch, and one of Chicago’s most popular Halloween time events, is most certainly Jack’s Pumpkin Pop-Up. This celebration of fall is one of Chicago’s most popular October events. It’s also the only one that takes place 100% outside.

This year there will be a corn maze, axe throwing, carnival games, food trucks, full bars, and much more fall fun, all spread out over 2 acres in Goose Island!

You can grab your tickets here

5. Pick out the perfect pumpkin

Talking of pumpkins, nothing is more representative of the fall nor is there something quite like a perfectly carved jack-o-lantern to get you into the mood for the spooky season. 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. We’ve put together a list of the best pumpkin patches in the area so you can pick out the perfect Chicago gourd!

6. Attend Chicago’s 2021 Vampire Ball

Resurrecting an American tradition, the infamous Chicago Vampire Ball returns this Halloween offering Chicagoans a fang-tastic evening of live entertainment! Get your capes on, your fangs out, and get ready for a vampire party like never before. From 8 pm – 2 am on October 30th a vampirical night will possess the Twisted Hippo Taproom and Eatery in Albany Park.

The eclectic evening will begin with a Vampire Queen Pageant and the coronation of Chicago’s newest Queen Vampire before an array of exhilarating entertainment will offer patrons of all shapes and sizes something to sink their teeth into. Including live burlesque performances, projected vampire movies, a retro pinball arcade, appearances by the Sensual Vampiresses of BimBamBoom, and a live DJ to keep blood pumping throughout the night.

You can grab tickets to the 2021 Vampire Ball here.

7. Brave the Old Joliet Haunted Prison experience

For those interested in a real thrill ride, outside of Chicago the huge Joliet Correctional Center, known colloquially as Joliet Prison, has opened as a haunted house just in time for the 2021 Halloween season and it looks utterly terrifying.

If you are fascinated by the tales of purportedly haunted places, get a buzz from exploring abandoned buildings, and wish to celebrate this Halloween with more than a costume party, this is for you. For there will be few Halloween experiences spookier than a trip to what will be Chicagoland’s first and only haunted house inside a real abandoned prison.

You can read more about this frightening experience here.

8. Check out the award-winning 13th Floor Haunted House

Rated as one of the Top 5 Haunted Houses in the U.S.A. by USA Today, 13th Floor Haunted House Chicago has officially returned from the grave for its terrifying eighth season in Chicagoland with a brand-new location.

Set amongst forty-thousand square feet of fun at 5050 River Road in Schiller Park near the Rosemont entertainment district, the new site features two all-new, scary-as-hell exhibits entitled Bad Blood and Spirit of Halloween.

You can read the full article here.

9. Catch a frightening flick up on Whiskey Business’ spooktacular rooftop

Along with haunted houses, watching some terrifying flicks are another essential element of Halloween. There’s nothing quite like grabbing snacks, getting comfortable, and sinking into the sofa for a horror. This Halloween you can take scary movie nights to the next level by trick or treating yourself to an evening full of spooks and scares at Whiskey Business’ rooftop movie showings!

Enjoy Halloween-themed cocktails with your friends on the rooftop and grab some popcorn for some classic Halloween movies on the silver screen. Turn up in your best costume and you’ll be in with a chance to win a prize!

Grab tickets here and see the Halloween lineup below:

Mondays, Tuesdays & Thursdays @ 7:45 PM
10/04 – Ghostbusters
10/05 – Hocus Pocus
10/07 – Beetlejuice
10/11 – Nightmare on Elm Street
10/12 – Nightmare before Christmas
10/14 – Candyman (The Original)
10/18 – I Know What You Did Last Summer
10/19 – Scream
10/21 – Seven
10/25- 10/28 – Double Feature: Hocus Pocus & Beetlejuice

10. Be stunned at West Loop’s Halloween speakeasy ‘Manifestations: The Art of Seance’

A chance encounter with a mysterious organization introduced magic historian, Jim Bergstrom, into the world of professional mystics and seances! Twenty years later, Jim is now spilling secrets and demonstrating techniques for private audiences. Learn all the tips and tricks of how séances were performed. Porkchop’s dinner and show experience Manifestations: The Art of Seance will leave you enthralled and enlightened.

Get your tickets now!

11. Dress up and drink up at a Halloween-themed bar crawl in Chicago

Are you ready to paint Halloweentown red? Calling all costume wearers, pop culture icons, and doppelgangers, take your crew on a spooky adventure all through Chicago and make it a night to remember. From dance parties, DJs, live bands to costume contests, there is something for everyone on this escapade that will leave you wanting more.

Get together a group of your friends and grab your tickets for 2021 Chicago Halloween Bar Crawl today.

12. Enjoy an eerie aquatic experience on the Chicago waterways

Some creepy cruises and bloodcurdling yacht parties are taking place this Halloween if you dare jump on board:

The 2nd annual Henny Halloween yacht party will be taking place on the Anita Dee yacht on Sunday, October 24th offering guests the chance to enjoy three floors of frightening fun on Lake Michigan. Turn up in your spookiest costume and boogie all night as live DJs play in front of the beautiful panoramic views of the city skyline.

A few days later on October 30th, you can join the Chicago River Halloween Boo Cruisefor a spooky adventure from Halloween afternoon past moonlight. Ghosts, vampires, goblins, werewolves, and more will join you on your journey along the Chicago River and out into Lake Michigan. If you’re all about Halloween, this is the place to be!

There will also be Halloween BOOze Cruises taking place Thursday 28th, Saturday 30th, Sunday 31st, Monday 1st on the Anita Dee II!

Grab tickets to either the Henny Halloween yacht party, the Chicago River Halloween Boo Cruise or the Halloween BOOze Cruises whilst they last.

13. Snap some spooky selfies at the Museum of Illusions

The Museum of Illusions and its many mind-boggling installations have been given an extensive makeover for the Halloween season offering guests an even more disconcerting experience than before.

Well-known exhibits including Head on a Platter, Vortex Tunnel, Infinity, and Anti-Gravity Room have been converted with Halloween-themed décor making the Museum of Illusions one of Chicago’s most immersive and mysterious go-to destinations for the Halloween season.

You can read the full article here.

14. Brew some delicious potions at home with this spooky spirit virtual mixology class

If you rather stay home this haunted holiday, may we suggest you try your hand at potion-making… we mean… cocktail making. Witchcraft! Spooky Spirit Virtual Mixology Class invited you to explore three mystical cocktail-making techniques featuring smoke, fire, and transmutation, whilst enjoying some other spooky surprises including live magic, musical guests, and more.

Order your kit here.

15. Peruse Navy Pier’s Pumpkin Lights event

Navy Pier has transformed for its month-long Pier Pumpkin Lights event. After the event was canceled last year due to the global pandemic the spectacle returns allowing guests to wander through nearly 1,000 elaborate jack-o’lanterns for the entire month of October.

The pumpkins, and a variety of pumpkin pop-up installations, will be on display from Friday, October 1, until Sunday, October 31. According to the Navy Pier website the “insta-worthy experiential fall spectacle” will be accompanied by other Halloween festivities throughout the month. The Pier Pumpkin Lights event will once again be completely free with no additional admission fees and many of the pier’s restaurants and bars will be offering special deals.

You can read the full article here.

16. 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 13! 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 more than 1,000 hand-carved pumpkins — with some weighing up to 150 pounds! The event will take place October 13 – 17 and 20 – 24 from 6:30 – 10:30 p.m.

Read more about it here.

17. Head to the zoo for Lincoln Park Zoo’s unique after-hours experience

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.

“Guests will enjoy unique animal chats, educational entertainment, a live DJ, and multiple bars throughout the zoo at this after-hours event. No kids. No crowds. Strolling among wildlife with a beer, cider, hard seltzer, or glass of wine in hand. Sound fun? Join us!”

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.

Read the full article here.

18. Treat yourself to a surprise Halloween dinner

Celebrate Halloween with an incredible surprise dinner by Find the Dinner! If you’re a foodie who loves a good surprise, this plan was made for you. Let them guide you, with transport included, to a surprise restaurant in Chicago. This gastronomic experience will be adapted to your tastes and preferences, so you’re sure to leave with a good taste in your mouth. Are you ready? Then don’t think twice!

Grab tickets to a Find the Dinner Halloween experience here.

19. Unwind with the undead at Recess’ apocalyptic ‘Army Of The Living Dead’ Halloween Party

If you’re familiar with West Loop’s Recess on 838 W. Kinzie Street, you’ll know that they make no little plans. When they throw a themed party they mean business. This Halloween season Chicago’s largest outdoor patio is throwing a one-night-only zombie party on Friday, October 29th.

The 14,500 -square-foot space and its surrounding 30 shipping containers will be transformed into an apocalyptic Las Vegas inspired by Netflix’s smash hit “Army of the Dead”. The cozy amalgamation of bars, food stands, and cabana houses found within will turn from a snug sanctuary to a surreal and shocking setup filled with blood-thirsty zombies.

You can read the full article here.

20. Shoot zombies with lasers at the Forge

The Forge: Lemont Quarries just outside of Chicago is loaded with action-packed entertainment for anyone and everyone to enjoy. In addition to an exhilarating mix of extreme sports, yoga courses, zip lines, nearly 300 aerial elements, climbing and bouldering walls, and a bike pump track — and many more awesome activities — the Quarries offers a series of tactical laser tag games.

With Halloween around the corner, the park has now resurrected its Zombie Apocalypse Tactical Laser Tag experience that offers out of this world fun for all.

“You’ll find yourself immersed in a post-apocalyptic world where a zombie outbreak has run rampant and wreaked havoc on the world,” the park writes. “The game will consist of two teams battling against each other while simultaneously fending off flesh-eating zombies. The team to earn the most points in the battle will survive to see another day.”

Read the full article here.

Jojo’s Shake Bar, famous for its over-the-top milkshakes and biggie hot chocolates, has elaborately decked out their adjacent patio in the heart of River North. The 5,000 sq ft space is now teeming with over 600 pumpkins, hay bales, and a bathtub filled with corn… just because.

If you’re a fan of those over-the-top milkshakes down at JoJo’s Shake bar make sure you don’t miss out on their gourd-geous Pumpkin Patch Shake. The one-month-only special comes topped with Pumpkin Pie Slice, Taffy Apple, Roasted Marshmallow, and Toffee Pretzel. Alongside this unique crowdpleaser, you can get your hands on some seasonal options like caramel apples, pumpkin pie, and spiked ciders.Admission is $10 per table and reservations can be made at jojosshakebar.com.

22. Sip on some spiked ciders

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.

You can find our list of the best spots for spiked ciders in Chicago here.

23. Work your socks off at a Halloween-themed fitness class

Trick, Treat, Tone or Tighten? If you’ve treated yourself to enough shakes and spiked ciders this month you might be interested in this amazing spooky-themed fitness class! You’ll want to make sure that your outfit is as terrifying as possible with awesome prizes such as $100 to use at Recess, West Loop, and a $25 Puma Gift Card. Bring out your finest zombie dance moves during the Thriller dance class or awaken your inner force during the yoga class.

Tickets and more information can be found here.

24. Roam the city for lost spirits

Of course, you can also take matters into your own hands and roam the city for lost spirits at your own pace. Chicago is an enchanting city, perhaps, more enchanting than 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 atsome of the most haunted places in Chicago.

Click here for a list of the 10 most haunted places in Chicago and get yourself into the spooktacular spirit!

25. Lose yourself in Richardson Farm’s ‘world’s largest’ corn maze

Richardson Farm in Spring Grove, Illinois, is home to a 28-acre corn maze that’s made up of tulips, sunflowers, Christmas trees, and an adventure farm. It may be located a fair bit outside of Chicago but it’s not too far to go for a maze holding the title of the largest in the world.

Featuring 9-10 miles of trails, Richardson Farm’s corn maze is in fact composed of 4 smaller mini mazes weaved together by the multiple meandering walking trails. In addition to their maze, Richardson Farm has a number of other attractions that include a 50-foot observation tower, a huge pumpkin patch, a community campfire, a zip line, zorbing — which is strapping into an inflatable 11-foot ball and bouncing down a hillside, a petting zoo, a giant slide, and much more!

You can read the full article here.

[Featured image from Unsplash / @szabojani]

See also: 60 Fantastic Things To Do In Chicago This October

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