This Halloween, celebrate with events, parties, and specials inspired by the 1893 Chicago World’s Fair, Olive Garden, true crime, New Orleans, and more.
Flight Club Embraces the 1893 Chicago World’s Fair
Thanks to the wild popularity of Devil in the White City, the 1893 Chicago World’s Fair is an aptly popular theme for Halloween hoopla. This year, Flight Club is embracing the theatrical/morbid era with a Halloween event filled with fortune-tellers, magicians, and murder mysteries. Be sure to dress in theme for a chance to win the costume contest. And come hungry for chicken skewers, flatbreads, and pumpkin spice cotton candy.
Details: October 31, 8–11 p.m.; $49
Tao Song Halloween at Young American
For one night only, Logan Square’s hippest new hipster bar is getting dolled up as a downtown-style nightclub, complete with fog machines and bottle service. Dubbed Tao Song, the shindig features a five-course tasting menu with dishes like langoustine crudo and Grey Goose cocktails bedazzled with 24-karat gold. After 9 p.m., it shifts to à la carte and club vibes.
Details: October 31, 6 p.m.–midnight; tasting menu is $60
Saint Lou’s Assembly Dresses Up as Olive Garden
Here’s a fun one: Saint Lou’s Assembly is embracing its inner Italian-American chain and slinging endless breadsticks for a few days this month. The decor will feature fake ivy plants, idyllic photos of the Italian countryside, and all the Frank Sinatra–style tunes you can dream of. To eat, the menu will boast fried ravioli, calamari, minestrone, tiramisu, breadsticks aplenty, and drinks like a frozen peach Be-Lou-ni and the Auntie Pasta Bloody Mary.
Details: October 30–November 1
Hopewell Brewing Company’s “The Void”
Later this month, Hopewell Brewing Company is getting celestial and rebranding itself as The Void, outfitting its contemporary space with a space-inspired balloon sculpture installation, magical illusions, and food from both Bang Bang Pie and Donermen. There will be special beer tappings of limited brews, and costumes are encouraged.
Details: October 26, noon–midnight; no cover
Halloween Drag Brunch at Tack Room
If you prefer your Halloween shenanigans with bacon and drag queens, then look no further then this upbeat offering from Tack Room. Pianist Kevin Eftekhari and drag queen Wanda Screw will be on hand to provide the Halloween-inspired entertainment and tunes, while food from adjacent sister spot Dusek’s Board & Beer will be served.
Details: October 26, 12:30 p.m.
Roaring Twenties Halloween Party at Artango Bar and Steakhouse
Prohibition-era cocktails, live cabaret music, and costume contests all star at Artango Bar and Steakhouse’s Roaring Twenties–themed Halloween party. Drink specials for the occasion include Aviations, Blood & Sands, Red Royals, and Derby cocktails, along with a bevy of Latin tipples. International cabaret star Tanya Melamed performs at 9 p.m., and a costume contest awards winners with gift certificates.
Details: October 26, 4 p.m.–1 a.m.
Voodoo Vibes at Ina Mae Tavern & Packaged Goods
Seeing as Ina Mae Tavern is an homage to New Orleans, it’s the perfect spot for Halloween and voodoo stylings. October 24–November 3, the Wicker Park haunt will host Ina’s Voodoo Lounge, a festive pop-up with tarot card readers, live music, pumpkin painting, Halloween trivia, a Nola-inspired happy hour, and even screenings of American Psycho and Nightmare on Elm Street. There will also be food and drink specials aplenty.
Details: October 24–November 3; events, times, and prices vary
True Crime Trivia at Chicken Shop
Halloween is the perfect time to celebrate America’s collective obsession with true crime. And Chicken Shop is going all in with this specially themed trivia night, wherein groups are encouraged to come test their knowledge on all things criminal, from Ed Gein and the Golden State Killer to Chicago’s own H.H. Holmes and John Wayne Gacy. The winning team earns a $100 gift card.
Details: October 30, 7 p.m.
Spicy Boy Karaoke at Ludlow Liquors
Candy and karaoke and cocktails make for a successful Halloween night, methinks. Avondale’s impossibly hip and fun Ludlow Liquors is keeping it refreshingly casual for the holiday, with Halloween-themed Spicy Boy Karaoke, plus plenty of drinks and snacks.
Details: October 31, 9 p.m.; no cover