Whether you’re in search of a fright or want to bring your best costume ideas to life, Chicago has a ton of one-of-a-kind events to get you into the Halloween spirit. Just for starters, you can step inside a horror movie museum, play carnival games at an adult pumpkin patch, dance with drag queens at a costume ball, and so much more. Check out some of the top parties, booze cruises, and pop-up experiences for the 21-and-up crowd to start planning your Halloweekend itinerary in Chicago!

Jacks Pumpkin Pop-Up
Jacks Pumpkin Pop-Up; photo courtesy WeLovePopUps.com

Jack’s Pumpkin Pop-Up on Goose Island
Visit a two-acre pumpkin patch in the heart of the city. Jack’s Pumpkin Pop-Up is a larger-than-life experience located on Goose Island. The massive outdoor experience has carnival games, axe throwing, three full-service bars, food trucks, fortune tellers, Chicago’s largest corn maze, and tons of photo opps. With a nighttime lights display and pumpkins galore, spend a crisp autumn evening outside at Jack’s. Open nightly this October. Tickets are available online for purchase.

Rooftop Asylum Halloween Party at I|O Godfrey
This fourth-floor rooftop will be transformed into a haunted asylum, complete with Halloween food and drink specials (like a charcuterie skull, toxic waste mac and cheese, or purple poison cocktail). Plus, the roof will be outfitted with nine haunted igloos, each decked out in spooky decor that fits a different Halloween theme. Reserve your spot today.

TILT Terror Nights at 360 CHICAGO Observation Deck
Get your thrills and chills while hovering more than 1,000 feet above Chicago. This Halloween event at 360 CHICAGO offers guests a special after-dark experience, featuring a longer and faster spin on their signature TILT ride. You’ll also find Halloween-themed cocktails and to-die-for city views. Get your tickets today.

Tarot Cocktails at The Gwen
Tarot cocktails at The Gwen

Haunted Halloween Ball at Congress Plaza Hotel
Dress up for Chicago’s largest and scariest Halloween costume party. Experience a night of thrills at the Haunted Halloween Ball on Oct. 30 at the (reportedly haunted) Congress Plaza Hotel. The massive ballroom of the 122-year-old hotel will transform into a zombie-themed dance floor where live DJs, vampire bellmen, and costumed go-go dancers rule the night. The event starts at 9 p.m. and goes until 3 a.m. Tickets are available for purchase online. 

Totally 80’s Halloween Party at Time Out Market
Swing by Time Out Market Chicagofor a Totally 80’s Halloween Party as the food hall travels back in time on Oct. 30. Drink a Pop Rocks-rimmed cocktails, jam to an awesome ’80s soundtrack, snap photos in front of giant Lite Brite, play Pac-Man, or set a high score on Super Mario Bros.

Afrofusion Halloween Party at The Promontory
Dance the night away at this Afrofusion Halloween Party on Saturday, Oct. 30. The Promontory in Hyde Park is hosting this costume content and dance party, where international DJs fuse hip-hop, R&B, reggae, and afrobeats into a one-of-a-kind musical experience. General admission tickets and table reservations are on sale now.

Lincoln Park Zoo; photo by Phil Parcellano

Adults Night Out at Lincoln Park Zoo
While zoo-goers might be familiar with Lincoln Park Zoo’s Fall Fest from Oct. 8 – 21, adults can enjoy an evening stroll among wildlife with a beer, cider, hard seltzer, or glass of wine in hand at Adults Night Out: The Great Pumpkin Glow. With multiple bars and no crowds, this after-hours event offers music from a live DJ, lawn games, and free rides on the Endangered Species Carousel. This special night takes place on Oct. 28 from 6:30 – 10 p.m. and tickets can be purchased online.

Tarot Cocktails at The Gwen
The Gwen Hotel, recently named the best hotel in Chicago by Conde Nast Traveler, will have a full menu of tarot-themed cocktails for October. They’ll also host Halloween events, like screenings of classic horror movies.

Haunted Halloween Booze Cruise
Celebrate Halloween on the water this year. Set sail from DuSable Harbor on a Haunted Halloween Booze Cruise aboard the Anita Dee I Yacht. With amazing skyline views, a full bar, and music, you can dance the night away in your Halloween best at this 21+ event. Enjoy the lake breeze on the open deck as you take in Chicago’s landmarks lit up at night. Costumes are encouraged and tickets can be purchased online.

Northalsted Business Alliance Halloween Parade
© Northalsted Business Alliance

Haunted Halsted Halloween Parade
For those looking for both fun and fright, check out the Haunted Halsted Halloween Parade on Oct. 31 at 6 p.m. This costumes-encouraged event celebrates its 24th year along Halsted in the Northalsted neighborhood. Think your costume might turn heads? Enter one of the seven costume contest categories and win $500 for coming in first place. Complete with an award ceremony and an after party, this crowd favorite event is sure to be a night to remember.

Rooftop Halloween Party and Drag Show 
Costume up and boogie down with the stars of RuPaul’s Drag Race at Marvin’s Food & Fuel in the West Loop. This special Haunt and Flaunt event on Oct. 28 is taking over the indoor restaurant and the climate-controlled rooftop. Admission includes a costume contest with prizes led by fabulous drag queens, premier DJs, a complimentary Halloween punch cocktail, and Halloween-themed movies projected on the big screen. Get your tickets today.

Uvae Kitchen and Wine Bar
Uvae Kitchen and Wine Bar

Halloween Murder Mystery Wine Dinner
Enjoy a classy evening of food, wine, and murder during this Halloween dinner party on Oct. 31 at Uvae Kitchen and Wine Bar in Andersonville. Guests will enjoy a five-course feast while trying to solve a mysterious murder. Costumes are encouraged, tickets are on sale now.

Gates of Hell Halloween at On Tour Brewing
For Halloween this year, On Tour Brewing Co. is hosting a Gates of Hell Halloween Weekend. From Oct. 28 – 31, the brewery will live stream the Las Vegas Halloween Phish shows starting at 9:30 p.m. each night. For a special Halloween themed celebration on Oct. 30, On Tour’s musically themed costume contest will kick off with live music from blues-infused jam band Downers Groove. Wear your best for a chance to win an On Tour prize and bragging rights.

Slasher Museum Pop-up at Replay Lincoln Park
Replay Lincoln Park is back with another immersive pop-up experience. They’re transformed their arcade bar into a museum for the macabre, with eerie replicas from iconic slasher films, including Halloween, A Nightmare on Elm Street, and The Texas Chainsaw Massacre. From now through Oct. 31, guests can compete in Halloween trivia, horror-themed games, and more.

Fright Night at Momotaro
The Izakaya, Momotaro’s subterranean lounge designed to mimic the Japanese nightlife, is transforming into the abandoned Tokyo Metro station Oct. 29 – 30 and serving up some vintage Japanese horror, specialty cocktails, and delicious dishes to shock and delight. Tickets are available online and must be purchased in advance.

Sweet Dreams Halloween Pop-up at Rizzo’s Bar
Attend a horror movie-themed pop up…if you dare. This October, Rizzo’s Bar & Inn is bringing your nightmares to life with a spooktacular indoor/outdoor Halloween pop-up. The bar will be decorated with epic Halloween scenes inspired by 20 classic horror movies, creating a massively twisted Halloween experience. The Sweet Dreams pop-up begins Oct. 8 and will be open throughout the month. Tickets can be purchased online.