The dog days of summer are gone and Halloween is fast-approaching. That means one thing — it’s time to grab a mask or costume and head to some of Chicago’s scariest and most creative seasonal parties. From Table, Donkey and Stick’s annual offal dinner to the Chicago Athletic Association hotel’s spooky Stephen King-themed circuit, these 17 hotspots are offering more than pumpkin beer and Monster Mash. Partiers who strut their stuff in costume may even win cash and prizes.Read More
The Ultimate Guide to Halloween 2019 in Chicago
These 17 spots have plentiful tricks, treats, and spooky scares
1. Young American
This Logan Square bar and kitchen will transform into Laotian restaurant/nightclub “Tao Song” on Thursday with bottle service, fog, and a $60 five-course tasting menu (langoustine crudo, dry-aged Slagel Farm strip steak, and more) from 6 p.m. to 9 p.m. Customers can revel on a hazy dance floor and order al la carte from 9 p.m. to midnight.
2. King of Cups
Chicago, IL 60614
A relative newcomer to Lincoln Park, King of Cups plans to go hard for the royalty-themed cocktail bar’s first Halloween season. Its “Seven Ways To Die” celebration runs through November 11 featuring “haunting vignettes” depicting the various bizarre deaths of royalty, as well as tarot card readings and $12 spooky drinks. These include “the Underworld” (blanco tequila, Pimms, carrot, lemon, egg white, soda, cinnamon) and the “7 Deadly Sins” (bourbon, Malort, house-made candy corn syrup, lemon, soda, sea salt).
3. Table, Donkey and Stick
Gourmands can put their palates to the test at Table, Donkey and Stick’s seventh annual offal dinner on Thursday. In true spirit of the season, diners can try a five-course dinner for $49 with dishes such as pig trotter poutine, rye blood noodles with lamb heart (guanciale, pickled tropea onion), and blood chocolate cake with plum ice cream.
4. The Violet Hour
This groundbreaking speakeasy-style cocktail bar in Wicker Park is throwing a masquerade for guests at $75 a ticket on Thursday from 8 p.m. to 11 p.m. Each ticket purchase comes with a Halloween slushy, as well as mini-tutorials on cocktail making, absinthe, herbology, and more. Staff will also serve spooky drinks off a special menu, along with light food items. Patrons are encouraged to dress in “mystical and ghoulish” costumes.
5. Ina Mae Tavern & Packaged Goods
Big Easy-style restaurant and bar Ina Mae Tavern continues to play on its New Orleans theme with the Halloween pop-up “Ina’s Voodoo Lounge,” which runs through Saturday, November 2. Ina’s offers a mess of events, including a “drive-in double feature” showing tonight of freaky films American Psycho (7 p.m.) and Nightmare on Elm Street (9:15 p.m.). On Wednesday patrons can attend Ina’s so-called drinking bee (“the spelling bee fueled by booze”) with $8 sangria and 18th Street beer. The main event comes Thursday with a half-price cocktail menu featuring drinks named for horror movie classics such as Evil Dead and Rosemary’s Baby, an “illusionist” presentation from 5 p.m. to 7 p.m., and a burlesque show at 9 p.m. Live music, tarot, and palm readings are available on Friday and Saturday.
Zoë Schor’s West Town fried chicken haven is back with its annual Halloween “Zombie Prom” on Thursday, this time with a ‘70s theme. Skip the cover and reservations — all revelers need to do is show up, hopefully in costume. Staff promise high school-y hits such as Jell-O shots and spiked punch, as well as karaoke all night long.
West Town’s German-Southern hotspot is taking on the guise of “Funkback Steakenhausen,” a playful take on global chain Outback Steakhouse, on Thursday for Halloween. Diners can anticipate twists on Aussie staples such as coconut shrimp “on the barbie,” a take on Outback Surf n Turf called “sürfenturfen,” and a dessert, “Chocolate Thunder from Down Under.”
8. Untitled Supper Club
Notoriously over-the-top River North venue Untitled also plans to bring a New Orleans-style Halloween to Chicago with “Nightmare on Bourbon Street,” a one-night event on Thursday. Representatives promise three rooms packed with contortionists, pole and burlesque dancers, circus performers, and live music from Mario Abney and his big brass band. Touted as one of Chicago’s “biggest live performance nights,” the event costs $10 per person at the door and patrons must be 21 or over. Bottle service and guaranteed seating are available by request.
9. Flight Club Chicago
Swanky bi-level dart bar and restaurant Flight Club is telling a hometown horror story on Thursday with a party styled after Devil in the White City, a non-fiction book that describes how Chicago serial killer H. H. Holmes used the chaos of the 1893 Chicago World’s Fair to slay men, women, and children. From 8 p.m. to 11 p.m., patrons can enter for $49 each or purchase a 10-diner package for $500. They can expect darts, an open bar, and a costume contest, as well as dishes such as flatbreads, vegetable dumplings, and pumpkin spice cotton candy.
10. RAISED | An Urban Rooftop Bar
This bar on the third floor rooftop of the Renaissance Chicago Downtown Hotel will lean into slasher film nostalgia on Thursday starting at 4 p.m. Representatives promise fictional fiends such as Freddy and Jason, along with a spooky set from DJ 5ive from 5 p.m. to 7 p.m. Creepy cocktails will also be available, such as the “O Negative” served in an IV bag (Vida mezcal, Domaine de Canton ginger liqueur, Amara blood orange liqueur, beet, lemon) and “the Creeper’s Peeper” topped with a lychee and cherry “eyeball” (Valentine elderflower vodka, Koval cranberry gin, lemon, egg white, cherry caramel drip).
11. Saint Lou's Assembly
West Loop spot Saint Lou’s has garnered media attention for its playful Halloween disguise: “Saint Olive’s Garden” will run Wednesday through Saturday, offering its take on the mostly-suburban Italian-American chain. Diners can expect fake plants, decorative plates, and a Frank Sinatra-laden playlist to go with white lasagna, fried ravioli, pasta, and — naturally — unlimited breadsticks. Italian drinks such as a house-made “Lou-mencello” and a frozen peach “Be-Lou-ni.”
12. Bad Hunter
This West Loop favorite will host “the Unbearable Charm Masquerade Halloween Bash” Thursday from 8 p.m. to midnight, a party that management promises will lead partiers through an “otherworldly maze of immersive environments” filled with tricks and treats. Tickets are $25 in advance and $35 at the door, and the price includes two cocktails and light food. Costumes aren’t mandatory but attendees are asked to don a mask, in keeping with the masquerade theme.
13. The Darling
Whimsical Randolph Street bar and restaurant the Darling hopes to lure diners down the rabbit hole at “Alice’s Wonderland of Horrors,” a Halloween pop-up on Thursday. For $45 per person for a 2 hour seating, diners can indulge and imbibe while engaging with performances throughout the space. The price includes a complimentary “welcome poison” and a Monkey 47 Gin drink.
14. Chicago Athletic Association
The Chicago Athletic Association hotel will make hay of the recent release of It Chapter Two Thursday with a Halloween celebration that draws on some of Stephen King’s greatest hits. Themed rooms will appear throughout the hotel: Game Room will be outfitted in the style of It with a DJ set from Audio Jack from 9 p.m. to 1 p.m. The Milk Room will serve the Shining-inspired cocktails, Stagg Court will feature a ticked screening of Carrie followed by a ‘70s-style senior prom, and the Cherry Circle Room will go retro as time-warped tale 11/22/63.
15. Lips Drag Queen Show Palace, Restaurant & Bar
Performers at the Near South Side’s new drag wonderland would never skip an opportunity for a killer costume, and thus “Deadly Divas” was born. Thursday’s Halloween drag show will feature a scary glamorous cast of queens and a costume contest with a $1,000 cash prize.
16. The Renaissance Bronzville
South Side bar and lounge Renaissance Bronzeville is offering Halloween party “Beautiful Nightmare Pt. 2” on Thursday from 10 p.m. to 2 a.m. The special patron with the best costume wins a bottle of Moet champagne at midnight, and partiers can purchase two bottles of Hennessy and Remy for $200, or two Don Julio and Patron Specials for $350. Cover is free and DJ Caleeb will provide the tunes.
17. The Promontory
The Promontory’s Hyde Park Halloween celebration is all about the costumes. Hosted by Kendra G, Leon Rogers, and Kyle Santillian of the WGCI Morning Show, “the Thriller! Halloween Costume Extravaganza” will run from 9:30 p.m. Thursday to 2 a.m. Patrons can show up in their sharpest outfits to win prizes in a range of categories. General admission is $20 in advance and $25 at the door.