You already know that Chicago’s Hallow-week is back. But if you think that’s the only major celebration for the spooky season, you sure don’t know what you’re talking about! Whether this is your first Halloween in Chicago or your twentieth, check out our top picks of things to do for Halloween in Chicago this year.PS: Looking for the hardcore scare? Head over to our Chicago haunted house list!
In the City
Jack’s Pumpkin Pop Up
1265 W Le Moyne St, Chicago, IL 60642
The space features endless entertainment and Instagram moments with larger-than-life installations to create the perfect pose with friends and family. There’s is no shortage of fun for all ages throughout the outdoor venue, featuring music and activities. Hit the bullseye at axe throwing, delve into mining for gems, search the corn maze for the one-of-a-kind hidden “boo”-zy bar or simply spend time sorting through the 10,000+ pumpkins to take home for the spooky season!
Pumpkin Carving Contest at County BBQ
1352 W Taylor St, Chicago, IL 60607
County BBQ, Chicago’s spot for the best smoked meats, sandwiches and more, is excited to bring back its annual Pumpkin Carving Contest. Taking place on Thursday, October 27th from 6 p.m. to 9 p.m., guests are invited to wear their best costume and bring their pumpkin carving skills! Prizes will be given for the best costume AND best carved pumpkin. Those who wear a costume will also receive a complimentary order of County’s delicious pork puppies.
Witches Brew at Masq
110 W Hubbard St 3rd floor, Chicago, IL 60654
Masq at Hubbard Inn is launching an immersive Hocus Pocus Experience called Witches Brew starting Thursday, October 13. Hosted Thursdays and Fridays on the 3rd floor, the Hocus Pocus Experience will feature live burlesque performances and variety shows, with two different seating times available to guests (6pm and 8:30pm). Tickets are $40 each and must be purchased in advance for the hour-and-a-half performances. There will be numerous photo ops, creative cocktails, and burlesque performances!
Dread Lobster at Heritage
Join in on the annual Halloween celebration as all our undead servers transform Heritage Restaurant & Caviar Bar into … Dread Lobster! From Tuesday, October 25th through Monday, October 31st, Heritage will feature special items like a chef’s “char-BOO-terie” board, a lobster roll, charcoal-roasted head-on shrimp skewers, and of course: cheddar biscuits (with togarashi butter).
Heaven & Hell Halloweekend at Radio Room
400 N State St, Chicago, IL 60654
Dineamic Hospitality’s music-inspired concept boasting incredible late-night performances, nostalgic vibes, and a creative menu serving up a “greatest hits” of crave-worth cuisine, will host a festive Heaven & Hell Halloweekend! All weekend long, beginning on Friday, October 28th through Sunday, October 30th, the party will feature a cocktail list and décor based on the Heaven & Hell theme. They’ll also feature live DJ music, musical performances, and more! Heaven & Hell cocktail specials include:
Haunted Homecoming at Barcocina
2901 N Sheffield Ave, Chicago, IL 60657
1814 W Chicago Ave, Chicago, IL 60622
Opening just in time for a Halloween, newly opened Barcocina West Town will face off against its Lakeview location with a North v. West Haunted Homecoming bash. At either location on October 29, celebrate spooky season with a 3-hour open bar featuring Mexican beer, house margaritas, signature cocktails, and wine. Entertainment includes a DJ, photo booth, a costume contest with a cash prize. Tickets are $50 and can be purchased separately for West Town and Lakeview locations.
Nightmare on Navy Pier at Offshore Rooftop
1000 E Grand Ave, Chicago, IL 60611
Creep it real this year at Offshore Rooftop. The frighteningly fun party begins Saturday, October 29 at 8 p.m. and runs until midnight, and invites guests to dress up in costume and enjoy a night filled with giveaways, a costume contest, a premium 4-hour open bar, passed bites, music, dancing, and more.
The cocktail menu will feature drinks with Grey Goose, Angel’s Envy, Patron, and Bacardi, the evening’s official sponsor. Blood bag “welcome cocktails” will be made available for guests upon arrival. To eat, guests can enjoy bloody buffalo bites with whipped bleu cheese, prosciutto and fresh mozzarella eyeballs, pumpkin soup shooters, mini salmon poke, hummus and crudité, grilled lamb lollipops, prime burger sliders, and mini vegetable egg rolls. In addition to frightening libations, Offshore will be overrun with décor with webs, spiders, skulls, and skeletons.
Beetlejuice Pop Up @ Redline VR
4702 N Ravenswood Ave, Chicago, IL 60640
Day-O! Redline VR is hosting a special pop-up bar for the recently deceased from Friday, October 21st thru Monday, October 31st! The Beetlejuice Pop Up Bar will feature 10 days of spooky cocktails, costumed characters, and photo opportunities. Entry is free but guests are encouraged to purchase VIP entry in advance. The $40 tickets include $30 of VR zombie shooting and a cocktail served by Beetlejuice himself! Tickets can be purchased here.
On Saturday, October 29th, Redline VR will be hosting a special costume contest from 9pm – 12am with live music and karaoke. The contest will feature $500 in overall prizes. Prizes include Best Group Costume, Best Overall Costume, and Best Beetlejuice-Themed Costume.
Tent Flix & Thrill at Lottie’s Pub
1925 W Cortland St, Chicago, IL 60622
Immerse in true Halloween spirit with movie screenings at Lottie’s Pub happening on Tuesday, Wednesday, + Thursday during the last two weeks of October. The first screenings will start at 5:30 PM for those looking to bring kids and family, which will then be followed by R-rated movie flicks starting at 8:30 PM. Movie screenings will take place in Lottie’s tents, so be sure to book your tent today at firstname.lastname@example.org
- Tuesday, October 18th-Thursday, October 20th | 5:30 PM: Hocus Pocus | 8:30 PM: Scream
- Tuesday, October 25th-Thursday, October 27th | 5:30 PM: Monster House | 8:30 PM: Scary Movie
Band Jazz Funeral at Ina Mae Tavern
1415 N Wood St, Chicago, IL 60622
For the rest of October, Ina Mae Tavern will transform into a Voodoo Lounge, offering Halloween-inspired specials + events all month long! For those who really want to experience true Voodoo magic, be sure to plan on visiting Ina Mae on Friday, October 28th. Following Ina Mae’s Happy Hour (half off Halloween cocktail menu), a strolling 4 Star Band Jazz Funeral will be right outside Ina Mae at 6 PM, sharing the electrifying tradition and energy of New Orleans with Chicago. Come witness the performance yourself and toast to another successful spooky season here in the city!
Ravenswood Costume Crawl
Your favorite Ravenswood haunts are teaming up for a ghostly new sweets and BOOze tasting stroll! Enjoy a fantastic selection of local desserts, candy, and beer and cocktail samples as you zombie shuffle between shops and restaurants along Montrose and Ravenswood Ave. Start by creeping over to Artifact Events (4325 N. Ravenswood Ave) for check-in where you’ll get a wristband, punch card, and map. Then you’re off to devour some treats. Costumes are HIGHLY encouraged and three lucky costumed attendees will score prizes from KOVAL Distillery. Tickets for the Ravenswood Costume Crawl are $25 in advance and include 10 tasting-sized portions of desserts and beverages, a Ravenswood canvas tote bag, and a few other goodies.
Anniversary Costume Party at Central Park Bar
2924 N Central Park Ave, Chicago, IL 60618
In celebration of their one-year anniversary this October, Central Park Bar in Avondale will host a Halloween costume party on Saturday, October 29 from 8 p.m. to 12 a.m. on the patio. Guests are encouraged to dress up in Halloween attire and the evening will feature drink specials like a $5 Frozen Spiced Latte (Misunderstood Ginger Spiced Whiskey, Maplewood Coffee Liqueur, oat milk, cookie syrup, and a cinnamon stick) and free photobooth photos for all. DJ ZZZosma will spin jams all evening and there will be prizes for best Halloween costume.
916 W Fulton Market, Chicago, IL 60607
Spend your Halloween in Chicago at Time Out Market, surrounded by delicious food, family-friendly activities, and a dog-friendly patio! Begin the celebration on Friday, October 28th with the Halloween Kick-Off Event from 6pm to 8pm, featuring a live performance by J Marks Trio. Meanwhile, the Dia De Los Muertos Halloween Party, which is the main costume party, takes place on Saturday, October 29th from 5pm to midnight. Looking for something fun with the kids? Come down on Sunday for the Kid’s Halloween Party from 10am to 1pm.
Morgan’s New Wave Halloween Party
952 W Fulton Market, Chicago, IL 60607
Now that summer is over and the dark days are here, it’s time for all of the moody ghouls to put on their tulle and gather for a night of tears and fears at Morgan’s New Wave Halloween Party. The event takes place Friday, October 28th from 9 pm to 1 am inside the three-story events venue and its retractable glass rooftop enclosure. The party features a plethora of a-ha moment activities, including a New Wave karaoke lounge, burlesque performances by the Hot Tawdry Troupe, and a sensationally opulent synth-centric dance party on their private glass-enclosed rooftop overlooking the West Loop.
Midnight Dance Party at The Owl
2521 N Milwaukee Ave., Chicago, IL 60647
Perfect for night owls and late night Halloween revelry, The Owl in Logan Square will host a Psychedelic Disco Punk Dance Party on Monday, October 31 that runs from midnight until 4 a.m. Party-goers can sip on festive fall beers like Southern Tier Pumking, Temperance Oktoberfest, Schlafly Pumpkin Ale, Hopewell Harvest Pale Ale, and Hofbräu Oktoberfestbier all night long.
Halloween Costume Party at KINGS
Join KING’s for a Hocus Pocus-themed Halloween Costume Party on Saturday, October 29th, beginning at 9pm! A DJ will be spinning new and favorite top hits and guests will be entered into a costume contest with 1st place winning $100 and 2nd place winning $50. So grab your group of ghouls for a spooky night of games at KING’s. You’ll also get to explore their limited-time spooky cocktails.
Howl-O-Weenie at etta
700 N Clark St. Chicago, IL 60654
IT’S TIME FOR OUR PUPPY HALLOWEEN COSTUME CONTEST! And yes, it will be as adorable as it sounds. Tickets get you a spot for your fur-baby in the costume contest, a pup menu, a pup party tote to-go featuring goodies from local farm-to-paw business Treats de Cuisine, a specialty cocktail for each human, with a patio table for dinner, and all the photo opportunities. The winner of ‘Best Costume’ wins a dinner for four at etta! RSVP now before spots are gone! ** Please include how many doggos will attend in the reservation notes and their Instagram handle!
Howl-O-Ween at Cody’s Public House
1658 West Barry Avenue., Chicago, IL 60618
Cody’s Public House in West Lakeview, known for being dog-friendly inside and out, will host a Howl-O-Ween Costume Contest. Guests are invited to come early for the Bears vs Cowboys at 12 p.m. and stay for the costume contest which will kick off at 3 p.m. Cash prizes will be awarded for Best Doggy Costume ($100) and Best Dog + Human Combo Costume ($200). There will be raffles benefiting Alive Rescue and a Halloween-themed drink menu. Specials will include $6 Tito’s Vodka, $5 Hop Valley beers and FREE Chicago Dogs.
Wag-o-Ween Dog-Friendly Market at Bosly’s
4011 N Ravenswood Ave Suite 108, Chicago, IL 60613
Dress up your pup and come trick-or-treat at Bosly’s Backyard! They’ll have 15 vendors offering your dogs lots of goodies including a pet-friendly Halloween-themed photo booth, mini massages, pet baked goods, custom drawings, doggy apparel, human apparel, accessories, and more! Have a dog that doesn’t like crowds? That’s ok! Come support small businesses and bring home goodies for them to enjoy at home.
Halloween Drag Show at Remedy
1910 N Milwaukee Ave, Chicago, IL 60647
To kick off Halloween weekend, guests can join Remedy in Bucktown on Thursday, October 27 for the “Spoopy Halloween” Drag Show hosted by diva Ranger Cheeks and the ever fabulous and fierce Marvette Devo and Candi Forest. Guests can enjoy Remedy’s half-price happy hour from 4 p.m. to 7 p.m before the drag show begins at 7 p.m.
Halloween Party at Emporium
2363 N Milwaukee Ave, Chicago, IL 60647
To celebrate Halloween, Emporium Logan Square will host its first-ever two-day Halloween hangout Oct. 29 and 30. This FREE event will feature Halloween frights, drink specials, exclusive t-shirts, art, food, costume contests, music, movies, giveaways and more. Guests who RSVP in advance will also receive 10 free game tokens.
Special guest vendors include:
- The Horror House – Chicago’s newest horror shop offering apparel, artwork, collectibles, paintings, comics, movies and more.
- The Brewed – A horror-themed coffee shop in the Avondale neighborhood of Chicago.
- Atomic Cotton – A fantastically freaky and scary-stylish t-shirt store.
- JC Horrorbles – Offering creepy custom and horror collectables.
- 12 Gauge Gore – Vinyl decals and vintage gore posters.
- Pretty Spooky Handmade – Handmade spooky, horror, sci-fi, comic and pop culture-themed apparel, accessories and decor.
- Adams Art Box – Traditional ink, watercolor and mixed media artist of all things horror.
- Glass by Gaston – A local artist offering original glass art pieces.
- Joe The Magician
- The Cryptic Closet – Horror, humor and pop culture-inspired clothing.
HOUSE OF TAO
632 N Dearborn St, Chicago, IL 60654
The River North restaurant and nightclub is going all out for venue-wide “House of TAO” Halloween festivities from Oct. 27-29. Located in the iconic and former Chicago Historical Society Building, the River North hotspot is rumored to be haunted already. TAO Chicago will be hosting the go-to party of the season on October 28 complete with photo moments (think their own version of an iron throne), standout DJ sets from Gordo and Slushii, and a costume competition. The decor will also complement the iconic building’s storied history and serve as the perfect backdrop for one of Chicago’s favorite holidays.
112 W Hubbard St, Chicago, IL 60654
Joy District will host a special performance from Sean Kingston on Friday, October 28. The popular River North club will be open on Monday, October 31, with a special costume contest. The winner receives their RENT paid for the month of November!
Around the Burbs
Halloween in Long Grove
Long Grove is going full-out this Halloween! Pets throughout the region are invited to claw into their best Halloween duds and howl at the moon at the annual Pet Costume Parade on October 16th! Meanwhile, their annual Halloween party for the whole family will be held at Brothers’ Field on October 21st.
Schaumburg Halloween Carnival
Kicking off at Wintrust Field on October 21, The carnival features two weekends filled with free family fun, featuring spooky rides, tasty treats, trick-or-treating, seasonally themed arts and crafts, a beer garden and more!
The carnival is hosting two premier food and beverage vendors – The Popcorn Wagon and Funnel Cake Trailer, who will serve classic carnival fare like funnel cakes, corn dogs, popcorn, cotton candy, nachos and more. Carnival ride wristbands can be purchased in affordable bundles each day, or you can opt for the new FunTagg ticketing system if you prefer to pay per ride.
Featured Image: Unsplash