Chicago is getting spooky. From massive costume parties and haunted attractions to immersive experiences, Halloween pop-ups, parades and everything in between, we’re rounding up the events you need to know about this Halloween season. Start planning your October now.

420 Frankenstein brings a cannabis-fueled twist to Mary Shelley’s classic monster story this Halloween season. From the creators of 420 Shakespeare, the live comedy combines theater, improvisation and an unpredictable performance format, with one actor consuming 20mg of cannabis during each show. Catch 420 Frankenstein every Saturday from October 3 through October 31 at The Second City’s de Maat Theatre in Chicago. Get tickets here.

Haunted Halsted returns to Northalsted for Halloween night on October 31, featuring a full day of Halloween festivities, food, drinks, vendors and live entertainment. The free, all-ages celebration leads into the annual Halloween Parade from 7–8 PM, followed by a costume contest and post-parade party. Expect elaborate costumes, neighborhood energy and $4,000 in cash prizes throughout Chicago’s Halloween celebration.

WAMI’s Boos & Booze returns for Halloween weekend with a two-day bar crawl across Chicago. Taking place October 30–31, the event brings together multiple neighborhood routes, local DJs, drink specials, complimentary shots and access to participating bars with one ticket. Costumes are encouraged as crawlers take over River North, West Loop, Lincoln Park and Wrigleyville for a full weekend of Halloween nightlife. Get tickets here.

Azure Presents: Azure After Dark – Halloween Edition is an 18+ Halloween nightlife party taking place on Friday, October 30, starting at 8:00 p.m. at Experience 868 in Chicago. The high-energy event features live DJ performances, immersive seasonal decor, and themed entertainment. Get tickets here.

The Centre at North Park in Franklin Park, Illinois, hosts Ghostbusters: The Haunted Market on Saturday, October 17, from 2 p.m. to 7 p.m. This family-friendly Halloween event features over 25 local vendors, photo opportunities with the Windy City Ghostbusters, live face painting, music, games, and complimentary goodie bags for the first 50 children. Admission and parking are free. Reserve a spot here.

HighQ: America’s Favorite Drug Test is a 21-and-over comedy game show at Chicago’s Bughouse Theater on Friday, October 2, 2026, at 9:30 p.m. Blending sketch, improv, and variety, the show features three teams competing before a live audience in a hilariously spirited battle of wits and physical challenges celebrating cannabis culture. Get tickets here.

Chicago’s LondonHouse hotel will host "Nightmare on Wacker Drive: Día De Los Muertos" on Saturday, October 31, from 9 p.m. to 1 a.m. The 21-and-over event spans the indoor LH lounge and rooftop. Admission features a four-hour premium hosted bar, live DJs, and skyline views. A midnight costume contest will award prizes, including an overnight hotel stay and New Year's Eve tickets. Get tickets here.

Chicago’s Lincoln Park Zoo invites adults 21+ to Zoo Brews: Howls and Growls, a Halloween celebration taking place October 23–24 from 6:30 to 10 p.m. Guests can enjoy craft beer and cider samplings, unlimited rides on the carousel and Ferris wheel, live pumpkin carving, and costume contests while exploring night habitats. Ticket purchases directly fund the zoo's wildlife conservation programs. Get tickets here.

Presented by Yas, and! Comedy, Poison is an interactive, 60-minute queer sketch comedy show running at Chicago’s de Maat Studio Theatre at The Second City. Set in Dr. Gift’s laboratory, audience decisions control which mysterious potions test subjects consume, driving comic meltdowns. Performances take place Saturdays on October 3, 10, and 17 at 9:30 PM. Get tickets here.

Arts in the Dark returns for its 12th annual Halloween Parade on October 24, 2026, bringing elaborate costumes, giant puppets, floats, music and performances to Chicago. This year’s free, family-friendly parade moves back to Columbus Drive from Balbo to Monroe, running from 6–8 PM. The event celebrates Chicago’s creative community and Halloween as the “artist’s holiday.”