Halloween in Chicago 2019

Your Spooktacular Guide to the Windy City’s Halloween Happenings

From Halloween parties to haunted housesHalloween in Chicago is one of the best holidays to celebrate in the Windy City. Whether you’re a local or a visitor, you’re bound to have some spooky fun at one of these events. This year Halloween falls on Thursday, October 31, 2019, so most Halloween Happenings are on the weekend before, October 25-26, 2019.  Here’s your complete guide to spooktacular fun this Halloween season from the Gray Line Chicago team. 

Jack’s Pumpkin Pop-up

1265 W Le Moyne St, River West/West Town

Until Nov 3 2019

Returning to a two-acre plot of land just west of Goose Island, Jack’s Pumpkin Pop-up saves you a trip to the suburbs by bringing a corn maze, thousands of pumpkins and an array of carnival games to the city.

Pier Pumpkin Lights

Navy Pier | Chicago, IL, Streeterville

Until Nov 2 2019

You’ll find nearly 1,000 glowing pumpkins spread across Navy Pier at the attraction’s month-long Pier Pumpkin Lights event. Stop by Polk Bros Park to visit the Juggernaut of Jack-O-Lanterns installation then head to the pier to take in five more pop-up experiences, all of which will be illuminated after dusk each evening.

Nightmare Before Halloween: A Tim Burton Experience

Headquarters Beercade River North, River North

Until Nov 3 2019

Headquarters celebrates Halloween with a pop-up devoted to one of the spookiest directors of all time. Visitors can explore installations inspired by some of Tim Burton’s most memorable films, including a Beetlejuice graveyard, sculpted shrubs from Edward Scissorhands and a barber’s chair like the one used in Sweeney Todd.

Pumpkin Party at Gallagher Way

Gallagher Way, Wrigleyville

Oct 24 2019

Bring the kids to Gallagher Way for an early Halloween celebration in Wrigleyville, where costumed attendees can trick-or-treat around the park and participate in a variety of activities.

Illumination Halloween party

Revel Fulton Market, West Loop

Oct 26 2019-Oct 27 2019

The annual Illumination Halloween party is just as bright as it sounds, with 1,200 lights, interactive installations and a laser show. Attendees will enjoy treats from Happy Camper, Elis’ Cheesecake and Stan’s Donuts, as well as plenty of beverages. More importantly, the event raises money for research of a rare genetic condition called retinal vasculopathy with cerebral leukodystrophy (RVCL).

Lyric Halloween Masquerade

Civic Opera House | Chicago, IL, Loop

Oct 26 2019

Spend a haunted evening in the Civic Opera House at the Lyric Halloween Masquerade, which raises money to support emerging operatic talent.

Spooky Zoo

Lincoln Park Zoo | Chicago, IL, Lincoln Park

Oct 26 2019

This fun and free alternative to trick-or-treating attracts more than 25,000 kiddos and their families to the zoo each year. The event features Ferris wheel rides, a corn maze, animal-enrichment activities, live entertainment and a pumpkin carver.

Haunted Halloween Ball

Congress Plaza Hotel, Loop

Oct 26 2019-Oct 27 2019

The Congress Plaza Hotel hosts its annual Haunted Halloween Ball, inviting costumed attendees to spend a night dancing and celebrating in a building that some claim is haunted.

Logan Square Halloween Parade

Illinois Centennial Monument, Logan Square

Until Oct 27 2019

Logan Square’s annual Halloween procession brings out costumed kids and adults from all around the neighborhood for a festive celebration. The parade begins at the Illinois Centennial Monument and marches south on Kedzie Boulevard to Fullerton Avenue before looping back to Lula Cafe for hot cider and cookies.

Alice’s Wonderland of Horrors

The Darling, West Loop

Oct 30 2019-Nov 2 2019

Whimsical restaurant, cocktail bar and flower shop the Darling embraces its spooky side during Halloween, hosting a theatrical dining (and drinking) experience that draws inspiration from Alice in Wonderland. Injecting the atmosphere of a haunted house with its usual dinner theater offerings, the Darling will feature eerie performances during its dinner service from Wednesday, October 30th through Saturday, November 2nd.

Northalsted Halloween Parade

Belmont Ave and Halsted St, Lake View

Oct 31 2019

Wanna see some of the best Halloween costumes in the city? Head to Boystown, where a procession of dedicated cosplayers show of their creations at this annual processions.

Basement of the Dead

Regularly ranked as one of the top haunted houses in Illinois by Halloween connoisseurs, Basement of the Dead is well worth the short drive to Aurora. You’ll find killer clowns, bloody nuns and other costumed creatures prowling the claustrophobic halls of this subterranean attraction.

HellsGate Haunted House

Enter a multi-level mansion filled with creatures, secret passages and a gigantic slide at the HellsGate Haunted House. You’ll spend 45 minutes navigating the spooky attraction—if you’re able to find the fabled skeleton key during your journey, your ticket it free.

Dungeon of Doom Haunted House

Located in an old briquette factory in Zion, Illinois (near Six Flags Great America), Dungeon of Doom prides itself on providing each attendee with a full 60 minutes of scares. The haunted house is best known for its Buried Dead or Alive attraction, which simulates the experience of being lowered into a grave.

Statesville Haunted Prison

Zombie Army Productions’ flagship haunted house sits 50 minutes southwest of Chicago, but serious thrill seekers will want to make the trip. Visitors enter the fictitious Statesville Prison, where they traverse 23 different cells filled with rioting prisoners.

13th Floor Haunted House

Run away from a demonic nun and explore a vault populated by terrifying monsters and demons at the 13th Floor Haunted House in Melrose Park. Keep your wits about you and try not to get lost in the horrific, detailed sets that make up this seasonal attraction.

Goebbert’s Pumpkin Farm & Garden Center

35 miles from Chicago
Fall fun is the name of the game at Goebbert’s in South Barrington, where you can not only pick up all the pumpkins your heart desires, but you can also put the kids on a wagon ride or check out the exotic petting zoo (seriously, there’s a giraffe). Before you head home, get lost in the corn maze and check out the pumpkin-eating dinosaur.

Bengtson’s Pumpkin Farm

30 miles from Chicago
Pumpkins, ponies and hayrides make Bengtson’s a perfect fall getaway. Arrive hungry for apple cider doughnuts, award-winning barbecue and funnel cakes, too. Then let the kids expend some of that pent-up energy on the Barnyard Dance Cow Coaster and in Kids Village. Get a snapshot for the fridge at the free selfie booth before getting back in the car.

Odyssey Fun Farm

30 miles from Chicago
This aptly named Tinley Park orchard offers a pumpkin patch, a 15-acre corn maze, a zombie safari hay ride, zip lines and so much more. In other words, don’t plan on a quick trip—you’ll want to spend the entire day at this massive farm. Check out the official website for weekly events throughout the season.

Need to arrange transportation for your group to one of these events?  Give Aries Charter a call at 773-826-2000. 

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