Tricks & Treats: 10 Ways to Do Halloween In Chicago

Whether you want a night of fright or family fun, find Halloween happenings around town

What’s made of pumpkin spice and everything nice? Halloween in Chicago! As one of the most haunted cities in America, this time of year is especially spooky in the city. The season offers a little something for everyone, whether you want to join the annual Halloween Parade in Boystown, head with the family to a pumpkin patch or attend a masquerade ball decked out in your favorite mysterious costume. There are plenty of ways to have a spooktacular time in Chicago—here are our favorites.


Even Fodor’s has named
 this annual celebration one of the best 10 Halloween events in the U.S. On October 31, head to Halsted Street 
in the northside Boystown neighborhood decked out in your best costume—remember drag queens are your competition—and vie for the coveted best dressed title to win a cash prize of $1,000.


The genius works of poet and storyteller Edgar Allen Poe aren’t meant to be read alone. On Oct. 26, the actors of Lifeline Theatre converge on the Glessner House Museum to perform creepy reenactments of “The Tell-Tale Heart” and “The Raven” among other classics.


Enjoy a "Halloween" double feature with back-to-back screenings of Michael Myers' classics at the Music Box Theater on Oct. 27. The evening begins with the original 1978 classic at 7:00 pm followed by the 2018 followup at 9:00 pm.


Go pumpkin picking, explore a corn maze, take a ride down a burlap sack slide or “swim” through the city’s largest corn pool. These are just a few of the treats you’ll find at Lincoln Park Zoo’s annual Fall Fest, a free, family-friendly autumnal celebration. Bounce houses, pumpkin carving and other crafts and activities are also part of the fun. Open through Oct. 27.


Chicago Botanic Garden really lights up the night Oct. 23-27 with this pumpkin-palooza. More than 1,000 gourds of all crazy shapes and sizes (up to 150 pounds!) are hand-carved. They’re then placed around the Gardens’ walkways for all to see. Snacks and cider will be available for purchase.


Get a first-hand look at some of Chicago’s most haunted hot spots—if you dare! Paranormal researcher Ursula Bielski leads the way with Chicago Hauntings tour options including the Archer Avenue Triangle & Resurrection Mary Tour, the Devil in the White City Tour and the Loop and River North Ghost Walk, among other options. Check the website for the schedule and book early!


Be a real phantom at the opera in this annual masquerade ball hosted by the Lyric Opera of Chicago on Oct. 26. In addition to a night of revelry and dancing, the event features live music from some of the city’s best DJs, an open bar, hors d’oeuvres and a costume contest.


“This is Halloween! This is Halloween!” Tim Burton’s beloved animated classic, “A Nightmare Before Christmas” turns into a live extravaganza Oct. 31 and Nov. 1 at the Auditorium Theatre. In addition to watching the flick on a jumbo screen, the Chicago Philharmonic will perform Danny Elfman’s iconic score in real-time in this hallowed space. Costumes are encouraged.


All aboard this ghost ship for a Halloween party you’ll never forget! The Spirit of Chicago Yacht is all decked out for the holiday on this special sail around the city skyline Oct. 26. Costumes are strongly recommended.


For a traditional scare, head to 13th Floor Chicago in nearby Melrose Park through November 9, which features terrifying characters and scenes based on pop culture and horror movies. It's notoriously one of the scariest thrills in Chicago.