October 2023 events calendar for Chicago

Navy Pier is the site of a spooky immersive experience this October. Guests will delve into the mysteries of a once-renowned genetic plant laboratory, now transformed by grief into the Garden of Decay, by donning headsets and exploring rooms while guided by actors. The experience has been meticulously crafted with help from talented local artists, who have infused unique elements into each room. Afterwards, you can check out a world of interactive art, themed vendors selling treasures, tantalizing botanical cocktails, tarot card readings and many more activities in the Garden of reCreation.

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Millie Bobby Brown, Keegan-Michael Key and Elle Key, Bob Odenkirk and Henry Winkler. You can see a full schedule of programming on the Chicago Humanities Festival website. 

The Chicago Athletic Association is throwing several spooktacular Halloween parties throughout October. Put on your best outfit for Masha’s Monster Mash, a karaoke costume party hosted by Masha Potato, on October 21. If you’re into spirits and witches, stop by on October 28 for Bazaar of the Occult to shop wares from 50 artists and makers, plus enjoy tarot readers and live performers. Finally, live up your ‘90s fantasies as the CAA transforms its White City Ballroom into a bold and elegant world for a Romeo + Juliet Halloween Ball on October 29.

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. 

Hosted at tropical bar Bamboo Club, this annual Halloween-themed extravaganza features a multi-level haunted house as well an upstairs bar serving spooky cocktails. Tickets for the haunted house (which is open to attendees ages 16 and older) are $20 or $30 for VIP, which includes a drink and express entry.

Rhapsody Theater welcomes two-time Stage Magician of the Year Rob Zabrecky for a series of limited-run shows through Halloween. The one-person performance—dubbed The Zabrecky Hour—is equal parts puzzling, peculiar and hilarious, entrancing audiences with magic, comedy, song and dance, and an out-of-the-box interactive experience. Expect to be wowed by enigmatic illusions and other mysterious surprises during the wonderfully strange show.

Embark on a 75-minute boat tour that explores Chicago's spooky past while winding through some of the city's most gorgeous architecture. The nighttime tour is hosted by a costumed tour guide who highlights infamous incidents and supernatural occurrences.

Test your knowledge of all things holy and haunted during Holy Ghost Bingo: God, Goblins & Games, an interactive comedy bingo show at the Greenhouse Theater where audience members get quizzed on Halloween and Catholic traditions alike. FYI: You'll actually be playing bingo for this one, so Halloween candy and other spooky prizes are yours for the taking. 

Head to the suburbs this Halloween season to check out the second annual Schaumburg Halloween Carnival, a seasonal fun fair that spans two weekends full of spooky rides, trick-or-treating, themed arts and crafts, and snack vendors, among other attractions. This year, Wintrust Field will also transform into The House of Creeps haunted house. Entrance to the carnival is free, but you can also opt to purchase ride wristbands for unlimited runs on Krazy Kabin, Matterhorn, Sizzler and other classic rides. Parking is $5 per vehicle.

This haunted Macabre-style cocktail event comes to town September 23 through the end of October. Guests are invited to dress up and roam around the historic Eleanor Robinson Countiss House, where they’ll find live performances, a surreal ghost story, music and flights of mini cocktails. There are three different ticket levels, with gold tickets granting expedited entry, five cocktail tastings and decadent French chocolates.

The Izakaya at Momotaro is back again with its annual Halloween party and this year, the space is transforming into a haunted cinema. Step into a world of spine-tingling vintage horror movies brimming with thrills while feasting on izakaya bites and an array of delicious desserts. The bar team is also creating a menu of special cocktails that pay homage to classic films. Tickets are $95 per person.

I|O Godfrey is transforming its fourth floor rooftop into a haunteed manor, filled with dark secrets, eerie encounters and ghostly sights at every turn. Guests can also book an igloo reservation that comes with expedited entry to the party and a bottle of booze, but general admission tickets are also available for those who prefer to wander around and explore dance performances, DJ sets and spooky refreshments.

Arr, matey! The world’s largest rooftop is transforming its expansive space into a haunted sunken pirate ship this Halloween. Put your best costume on and prepare to walk the plank—the evening will feature a four-hour open bar, passed bites, a costume contest and plenty of dancing.

Celebrate Halloween at this lavish party hosted by LondonHouse Chicago, where you'll find a premium bar and live DJs spread between the LH on 21 Lounge, Etoile Ballroom and rooftop space. Stick around for the costume contest that commences at midnight—the first place winner will receive an overnight stay at the hotel and two tickets to the upcoming New Year's Eve party. 

Have a witchy night in Pilsen at this booze crawl throughout the neighborhood, where attendees can sip samples of beer and cocktails from 10 local bars and restaurants while enjoying live music and DJ tunes. Proceeds go toward Pilsen Fest, the neighborhood's annual summer street festival.

Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog (or cat) owners bring their costumed pets for a parade around the premises. The best-dressed furry friend is chosen by Alderman Brian Hopkins and Maureen Schulman and will receive prizes, but rest assured that everyone is a wiener! 

The Congress Plaza Hotel hosts its annual Haunted Halloween Ball, inviting costumed attendees to spend a night dancing and celebrating in a building that some claim is haunted. Guests will be able to mingle with spirits and the not-yet-deceased in the hotel's ballrooms, which sport spooky decorations, zombie cocktail servers, go-go dancers and vampire bellmen. You'll have access to multiple cash bars, great views of the city's skyline and the chance to enter a costume contest and compete for $2,000 in cash and prizes.

See the Blue Man Group with a touch of spooky (yet family-friendly) flair during these special Halloween weekend performances, where kids and their families are invited to show up early for pre-show face painting, Halloween surprises and goodie bags for little ones who wear costumes to the theater. After the performance wraps up, head back to the lobby for photo ops with the Blue Men themselves.

Wanna see some of the best Halloween costumes in the city? Head to Northalsted, where a group of dedicated cosplayers shows off their creations at this annual procession. You'll find drag queens, kids, parents and pets marching in the Halsted Halloween Night Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." The parade steps off at Halsted and Belmont at 7:30pm and heads north before ending at Halsted and Cornelia at 8pm; stick around afterwards, because the awards show commences at Halsted and Brompton at 8:30pm.

Based on the family-favorite board game, this new immersive and interactive experience puts guests into the roles of beloved CLUE characters as they try to solve a murder mystery. The game starts at Block 37, where detectives are greeted by the Butler before being sent on their way to gather clues from popular Chicago sites and shops. You’ll be tasked with finding long-lost antiques and figuring out who did it, where and with what.

Family retail and entertainment company CAMP has launched a 7,500-square-foot interactive shop-and-play experience in Lincoln Park. The Chicago location features the global debut of Doodles x CAMP—a colorful, comedic adventure created in collaboration with multimedia brand Doodles. Kids can crawl through tunnels into the glowing, mushroom-filled Lost Caves; zip down a rainbow slide; make an arts and crafts masterpiece under 12-foot-tall daisies in the Flower Forest; and more. There’s also a "Canteen" shop filled with toys, clothing, accessories and crafting stations.

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. The Doane Observatory is also home to the largest public telescope in the area, and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

Rooftop Cinema Club, the open-air theater perched atop The Emily Hotel, is back for a second season. Guests can catch showings of hand-picked classics, cult films and recent releases while also enjoying sweeping views of the skyline and craft beverages. It’s the perfect summer cinema experience.

Game Gamespace, a museum dedicated to video games, unveils a new exhibit featuring the iconic arcade game Q*bert. A playable version of the original game will be on display alongside the Parker Bros board game, concept design documents, photographs, art by creators Warren Davis and Jeff Lee, and an array of licensed Q*bert artifacts. There will also be an interactive sound station where visitors can play with the Votrax speech synthesizer that generated Q*bert’s incoherent outbursts.

Displaying a 25-story-tall video installation on the side of the Merchandise Mart, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place from May through October.