Chicago’s Coolest Halloween Parties and Events This Month
The only frightening thing this Halloween would be missing any of these amazing events.
Fall in Chicago is here, which means we only have about a month before our city freezes over and we all go into hibernation until the sun comes back out in late April. It’s painful, yes, but there are ways to blunt the blow. Specifically, now that it’s 12-foot skeleton season, it is your solemn duty as a Chicagoan to take part in as many of the city’s Halloween festivities before wrapping yourself in that weighted blanket for a few months. We’ve collected the city’s most special, spectacular, and spooky happenings for you, so be sure to take part.
Saturday, October 29
State Street between Lake and Van Buren
One of the best nights of the year returns to downtown as Arts in the Dark makes its way down State Street with all manner of weird floats, giant puppets, and oddball creative performances that will totally freak you out—in a good way.
Cost: Admission is free
Saturday, October 29
Congress Plaza Hotel
For the infamously haunted Congress Plaza Hotel’s 2022 Halloween Ball, they’re pulling out all the stops and transforming their 20,000 square-foot ballrooms into zombie-run abandoned hotels. Put on your Halloween finest, and expect a VIP experience, complete with encounters with the hotel staff: vampire bellmen, zombie maids, and costumed go-go dancers.
Cost: $20 - $1,000
October 22, 28, 29, and 31
Various River North bars
For those among us who deem bar crawls “essential,” there’s this River North crawl hitting up spots like Joy District, Hubbard Inn, LiqrBox, and more with themed drinks, a costume contest, DJs, and a digital bar map.
Cost: Tickets run $15 per person; additional menu prices vary
Monday, October 31
Halsted from Aldine to Waveland
Bust out your finest costume for the 25th edition of an all-sensory spectacle. Make your way down Halsted in Boystown with a Grand Marshals-led Halloween parade featuring not one—but five—costume contests, plus live performances from Molly & Alex and Brady Prince.
Now through Sunday, October 31
1465 N. Elston
It’s kind of weird to call this a pop-up when Jack’s Pumpkin Pop-Up has taken over almost the entirety of Goose Island, but here we are. Nomenclature aside, Jack’s Pumpkin Pop-Up’s sheer size means that it mimics the feel of a rural harvest festival smack dab in the heart of the city. Attractions include plenty of Instagram-worthy photo backdrops, apple cider donuts, take-home pumpkins, Chicago’s largest corn maze, multiple full bars, axe-throwing, and axe-throwing. I know we mentioned axe-throwing twice, but trust me, you’ll be thanking us for reminding you to get your practice in when you’re staring down a hockey mask-wearing murderer wielding a machete.
Cost: Tickets start at $25 per person for admission + corn maze ticket, add-ons are available
Now through Sunday, October 31
The holiday lights at Navy Pier get a lot of press (and for good reason), but don’t sleep on their Halloween-themed Pier Pumpkin Lights display. Somehow still flying under the radar for locals despite being the city’s most infamous tourist trap, Navy Pier is once again transforming into an Insta-friendly seasonal spectacle with multiple awe-inspiring pumpkin creations on display plus a variety of pop-up installations and specials throughout the pier.
Cost: No cover; additional costs vary
Thursday, October 27
Lincoln Park Zoo
The Great Pumpkin Glow is a Chicago Halloween mainstay for a reason. Dotting the zoo with cash bars, pumpkin patches, and corn mazes, while at the same time barring all those loud, meddling kids from entry turns the best zoo in America into a beautiful fall refuge. There's also a live DJ, haunted trail, lawn games, and even animal chats if you’re so inclined.
Cost: Tickets start at $15 per person
Saturday, October 22
This is the fifth anniversary of Gallagher Way’s huge, family-friendly party right outside Wrigley Field. The Pumpkin Party brings tons of fall-themed fun to Gallagher Way, including candy stations, lawn games, spiked hot chocolate for the grownups, balloon animal artisans, and even a roving magician. This year, as a special treat, the Old Town School of Folk Music will be there as well to lead folksy Halloween sing-a-longs, and Kid Create Studio will be teaching kiddos how to create paper ghosts or their very own Halloween slime.
Cost: Admission is free; additional costs vary
Friday, October 28
Logan Square Auditorium
Need a break from the be-costumed Halloween festivities? Craving something a little more hard-hitting? Swing by Logan Square on Friday night for a jam-packed evening of pro wrestling courtesy of WrestlePro. This is WrestlePro’s Chicago debut, and they’re bringing the heat by featuring legends like Colt Cabana, Lena Kross, Tommy Dreamer, and Scotty 2 Hotty. Better yet, all proceeds from the show will benefit The Hope For Us Network, and their suicide prevention programming.
The Music Box Theater
October 28 - 31
It’s back. The Chicago home of Rocky Horror Picture Show has finally brought back their legendary Halloween screenings, complete with shadowcasts where live actors perform the film in front of the screen. Trust us, it’ll all make sense when you get there. Get your tickets early — the Halloween screenings always sell out — and prepare yourself for an experience unlike any other. You’ll never be the same again.
Cost: $15 ($12 for Music Box members)
Replay Lincoln Park
Now - Nov 1
This year, the artists at Replay Lincoln Park are outdoing themselves by hosting not just one, but two Halloween pop-ups. Upstairs in their Level Up Bar, they’ve completely remodeled into a faithful recreation of the Springfield featured in Treehouse of Horror episodes, complete with a Raven Bart, Blob Homer, an inside-out living room scene, and plenty more photo ops and themed drinks. They’re also hosting Simpsons Trivia as well! And if that’s not quite your style, descend the stairs to visit Stranger Bar, a pop-up themed after the most recent season of Stranger Things.
Cost: Free, reservations available online (not required)