The best Halloween events and parties in Chicago

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing. 

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Abyssa’s Obsession made with pumpkin-infused rums, and the tequila-based Bone Temple. Want to recreate the creepy vibe at home? Several of the drinks are served in Halloween glassware that’s available for purchase onsite.

LondonHouse Chicago is hosting a spooky evening of Halloween fun across two unique spaces: The stylish LH on 21 Lounge and the iconic LH Rooftop, each offering a festive carnival atmosphere with eerie surprises. Guests will enjoy a premium open bar from 9pm to 1am and live DJ entertainment all night. There will also be a costume contest at midnight. The winner will receive an overnight stay at LondonHouse and two tickets to the hotel's New Year’s Eve event.

The Second City is reviving its annual Halloween series for a third time with Travel Can Be Murder, a 90-minute, unscripted whodunit inspired by Murder on the Orient Express and Death on the Nile. Based on a single audience suggestion, performers build a live, on-stage mystery that the audience must solve before the final line. 

Halloween in Chicago brings immersive attractions to surrounding towns around Illinois, where actors and set designers work hard to make you scream by forcing you to face your fear of clowns, cemeteries, snakes and other creatures that go bump in the night. Some of these haunted houses offer a full night of fun with bars, food trucks and escape rooms, so if you’re up for a good scare, buy a ticket to one of the best haunted houses near Chicago.

Wanna see some of the best Halloween costumes in the city? Head to Northalsted, where hundreds of people show off their creations at this spooky festival and procession. During the day, a street fest features food, drinks, live entertainment and more. At 7pm, you'll find drag queens, kids, parents and pets marching in the 30th annual Halsted Halloween Night Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." Stick around afterwards for the costume contest awards ceremony.

Six bars from Mexico City are popping up in River North this Halloween for Three Dots and a Dash's Terror in the Tropics: Midnight in Mexico celebration. The bars will each be pouring signature cocktails all night at Salon 61, where guests (who are encouraged to come in their best costumes) can enjoy DJ sets and the five drinks included with a GA ticket.

Hosted at Stolen Saddle—one of Chicago's largest country bars—this annual Halloween-themed extravaganza features photo ops galore, plus an upstairs bar serving spooky cocktails like Freddy’s Tequila and Darcula's Blood. There’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.

Explore Chicago's eerie past as you snake down the river aboard the First Lady Creepy Cruise. The 90-minute tour combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.

Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway, where other entertaining characters and activations await visitors. This year, a new 20-foot inflatable sculpture called "Monarch Skull" by artist Alyse Gamson joins the Garden's elaborate Halloween takeover. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

The Haunted House Party is back at the Shedd Aquarium, bringing together house music and Halloween for a spooky night to remember. Despite the event's name, there will be no scares here—the event's vibe is decidedly more "house party" than "haunted." Guests aged 21 and up are invited to come dressed in their finest costumes and dance the night away to sets by DJ Gent Hunt and DJ Heather.

Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog and cat owners bring their costumed pets for a parade around the premises. The best-dressed furry friend—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive prizes. Donations support the dogs, cats, kittens and puppies residing at PAWS Chicago.

This annual (and free) arts-centric Halloween parade returns to Columbus Drive for an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, youth programs and aspiring artists march from Balbo Drive to Jackson Boulevard. 

Guitar for Guaraldi is an annual free concert celebrating the work of Vince Guaraldi—the American jazz pianist best known for scoring the television adaptations of the Peanuts comic strip. Throughout the night, the Mich Shirley Trio will perform true-to-form guitar arrangements featured in It's the Great Pumpkin, Charlie Brown. 

In addition to the regular Arts in the Dark parade on State Street, the arts organization LUMA8 is hosting a "reverse" parade—in which attendees pass through a stretch of costumed performance groups lining Russell Drive in Washington Park. Bonus: At the end of the route, attendees will get a complimentary candy bag and other goodies. Come wearing your best Halloween costume!

Take the little ones trick-or-treating in Lincoln Park for some Halloween fun this spooky season. Businesses along Lincoln Avenue from Diversey Parkway to Webster Avenue on Saturday; and along Clark Street from Armitage Avenue to Diversey Parkway, and on Diversey Parkway from Lakeview Avenue to Orchard Street on Sunday will hand out candy to trick-or-treaters, so come dressed in costume. There will also be a special Halloween celebration at Lincoln Common Plaza on Saturday with a DJ, face painting, a photo booth, a balloon artist and more.

Maybe you don’t love pumpkin spice lattes or pumpkin pies, but it’s hard to deny the appeal of choosing your own perfect-to-you gourd at a pumpkin patch. The best pumpkin patches near Chicago are within an hour-and-a-half drive from the city (one is even in Chicago), and promise lots of Halloween fun.

Sanctum returns for another weekend of dark music, dancing and community at Thalia Hall and its piano lounge, Tack Room, this Halloweekend. Sanctum prides itself on standing head and shoulders above other music festivals, bringing in extra sound support from Big Audio, decking the room with curated decor and offering an “ALL VIP” ticketing concept that grants all attendees the same level of access. This year's lineup includes A Split Second, Buzz Kill, Pink Stiletto, Grave Love and more, plus a VHS Dungeon Room, photo booths, vendors and more.

Whether it's on a minibus or on foot, this tour takes you to the locations frequented by some of Chicago's most notorious gangsters and the places that have been haunted by their ghosts. With four tours offered daily, there's always an opportunity to take a step back in time to learn about figures like Al Capone and Chicago's haunted history.

Chicago Seadog offers a spooky ride down the river and lake this season with its Haunted Tours. The 75-minute tours, offered on Fridays, Saturdays and Sundays through October, are moderated by a costumed guide, who shares the eerie history of supernatural occurrences in Chicago. Guests (and their dogs!) are encouraged to come in costume and BYOB if they want to get boo-zy on board.

We've traveled just outside of Chicago to nearby suburbs to find a wide array of farms and orchards that have creative—and sometimes daunting—corn mazes to get lost in on Halloween. So make the most of the spooky season with a fun-filled day at the best corn mazes near Chicago.

The team at Fulton Market restaurant Ever is hosting a 1980s-themed Halloween soiree across three spaces: After, The B-Side and The Canvas by Ever. A ticket to this spirited evening includes food and drinks, plus access to all three spaces throughout the evening. Each venue will transform into a different retro-inspired haunt, featuring horror film references, music and Michelin-level fare.

What's better than dressing up on Halloween? Dressing up your pups, of course! This spooky season, the Howl-O-Ween Canine Cruise aboard First Lady is back for a limited-time, 90-minute lake and river cruise. Costumed dogs (and humans!) are invited to board the cruise to enjoy a narrated journey complete with pumpkin-flavored dog treats and a canine costume contest. The winners will be entered to receive a grand prize of a $1,000 check made out to a canine organization in the winner's name.

The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.

The city’s suburbs and surrounding countryside are full of bountiful orchards where you can pick pounds upon pounds of the fruit to take home for snacking or baking (speaking of baking, many of these farms feature bakeries stocked with homemade, apple-filled treats). If you're celebrating with little ones, these orchards offer plenty of Halloween fun for the whole family.

Make your Halloween a little BOO-zier with the Ravenswood Costume Crawl, which invites costumed attendees to stroll along a route stocked with local desserts, snacks and drinks samples on Montrose and Ravenswood Avenues. After the crawl, head to Koval Distillery for an afterparty with a costume contest, tarot readings and more.

Round up your family for a wild, multi-week Halloween festival at Brookfield Zoo. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including gorillas, goats and lemurs—to pumpkins that they can play with, nibble on and smash. 

Take a spooky step back in time to the age of Oak Brook's early settlers at the annual Cemetery Walk through Bronswood Cemetery. Guides will lead small groups down a half-mile path illuminated by lanterns as they share the tales of the community's pioneers. The one-hour walk includes a rest at the halfway point where guests can take a break and enjoy complimentary refreshments.