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Arts in the Dark
Photograph: Neal O'Bryan

October 2023 events calendar for Chicago

Plot out your October in Chicago with our calendar of things to do, including the best festivals and Halloween parties.

Jeffy Mai
Edited by
Jeffy Mai
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The official start of fall in Chicago might be in September, but the season doesn't really hit its stride until October—a month replete with crisp air, colorful fall foliage and a heaping helping of spooky fun. Take advantage of everything autumn has to offer by exploring the best pumpkin patches near Chicago, attending an apple-themed neighborhood fest, getting lost in corn mazes or staring up at the changing leaves at your local park or garden. And of course, celebrate Halloween in Chicago with spooky pop-ups, haunted houses, horror movie marathons and even more ghoulish events. Ready to embrace autumn? Check out the rest of the best things do to in Chicago this October. 

RECOMMENDED: Events calendar for Chicago in 2023

Featured events in October 2023

  • Things to do

This festival honoring and amplifying the voices and contributions of Indigenous peoples will take place at Wicker Park's Chop Shop over two days. Attendees will be able to immerse themselves in Indigenous music from Canada, the United States and Latin America, with performances by Digging Roots (Canada), Keith Secola (USA), Novalima (Peru), OPLIAM (USA), Raye Zaragoza (USA) and more. There will also be various engaging activities, craft demonstrations and interactive workshops. Admission is free but guests are encouraged to reserve their tickets online.

  • Things to do
  • Lincoln Park

Some of Chicago’s best chefs, breweries, wineries and distilleries are coming together for an evening to raise money and awareness for scleroderma, an autoimmune disease that causes thickening and tightening of skin. Sample bites and beverages from Bayan Ko, Smoque Steak, Fioretta, Le Select, The Publican, Swift & Sons, Pompette and more.

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  • Things to do
  • Loop

IES Abroad, a not-for-profit organization based in Chicago that provides college students access to more than 130 study abroad programs around the world, hosts this annual festival to celebrate student filmmakers who have created short films inspired by their study abroad experiences. The evening will feature screenings of the three finalist films, a Q&A with the creators, the reveal of the winner and an awards reception.

  • Things to do
  • Festivals
  • Loop

Want to get a free, behind-the-scenes look at the Chicago Board of Trade Building, Walt Disney's birthplace home, Orchestra Hall at Symphony Center and more iconic buildings throughout the Chicago area? You’ll have a chance to do so when the Chicago Architecture Center’s annual festival Open House Chicago returns to the city, opening up more than 170 architectural wonders across the city for free tours. Check out new additions like the Chicago Shakespeare Theatre and Riviera Theatre, or visit returning favorites such as Wintrust's Grand Banking Hall.

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  • Things to do
  • United Center

Watch world-class sommeliers do their thing at this vino-fueled tournament, which turns wine tasting into something of a competitive sport. The event kicks off with a free-range Tailgate Tasting event, where guests can sample from dozens of the world's best wineries and graze on endless bites. Then, competing sommeliers will face off in a six-round challenge of blind tastings judged by a panel of wine professionals, with a first place prize of $25,000 cash on the line. May the best palate win!

  • Things to do
  • Loop

Dress for Success' annual fundraiser returns for an enchanting evening of wine, cocktails and fashion, all while overlooking the picturesque Lake Michigan and the iconic Chicago skyline. Guests will be able to enjoy small bites from award-winning chefs and a host of beverages as models grace the runway. Purchase VIP tickets for exclusive experiences like hair and makeup touch-ups by Ulta Beauty and early shopping access.

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  • Restaurants
  • Lower West Side

The annual fundraiser for Meals on Wheels brings together 50+ chefs and bartenders for an evening of tastings and revelry. The night kicks off with a cocktail reception before a six-course seated dinner with pairings that's prepared tableside. Proceeds benefit Meals on Wheels, which delivers meals to people in need.

  • Movies
  • Loop

Some of the latest and greatest movies to hit the festival circuit arrive in the Midwest during the Chicago International Film Festival, which presents a lineup of more than 100 dramas, documentaries, comedies and foreign films, plus 60 short film programs. In addition to CIFF's home base at AMC Newcity 14, the fest offers viewing opportunities across the city, with screenings at the Music Box Theatre and the Gene Siskel Film Center. This year, the festivities will kick off with a free block party on Southport Avenue on October 11—in front of the Music Box Theatre—featuring live music, outdoor screenings, food vendors and moreYou can find a complete list of films, purchase tickets and learn about other programming on the Chicago International Film Festival website.

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  • Things to do

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

  • Things to do
  • Festivals
  • River West/West Town

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. 

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  • Things to do
  • Quirky events
  • Wrigleyville

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.

  • Things to do
  • Walks and tours
  • Streeterville

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.

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  • Theater
  • Comedy
  • Lincoln Park

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. 

  • Things to do
  • Festivals
  • Suburbs

Round up your family for a wild, multi-weekend Halloween festival at Brookfield Zoo that's perfect for all ages to enjoy. 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 capybaras, polar bears and gorilla—to pumpkins that they can play with, nibble on and smash. 

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  • Attractions
  • Parks and gardens
  • Suburbs

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. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

  • Things to do
  • Quirky events
  • Suburbs

Already got a jack-o'-lantern carved up at home? Ogle unique, hand-blown glass pumpkins made by 17 artists during the Morton Arboretum's annual glass pumpkin patch. The multi-day event lets guests watch glass blowing demonstrations, meet the artists and buy their very own glass pumpkins from October 13-15. 

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  • Attractions
  • Theme parks
  • Suburbs

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.

 

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  • Movies
  • Horror
  • Wrigleyville

This annual celebration of scary films returns to the Music Box Theatre for a 24-hour marathon of frightening, thrilling and chilling movies. Catch screenings of films like Child's Play 3, Candyman, REC and many others—you can see a full schedule here. One pass allows you to come and go for the duration of the spooky fest. Can't make the marathon event this year? The theater will be playing scary movies all month long.

  • Things to do
  • Festivals
  • Loop

This annual arts-centric Halloween parade returns to State Street to cap off the City of Chicago's "Halloweek" festivities with an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, inspiring youth programs and aspiring artists in every field march down the downtown thoroughfare and prepare for a spectacle. Plus, Arts in the Park is bringing back its "upside down" parade in Washington Park—where attendees can walk through a route thronged by costumed performers and puppeteers.

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  • Things to do
  • Quirky events
  • Suburbs

Outfit a "casket" (i.e. casket-shaped cart with wheels) in your favorite decor for this spooky annual race through the streets of downtown Forest Park, now in its 11th year. The rules are simple: A helmet-clad "ghost" rides inside the casket, while runners push the contraption as fast as they can along a 585-foot course. Prizes will be awarded for casket decorations as well as for the winners of the race, but try not to worry too much if you're not particularly athletic—there's also a prize for the "dead last" final finisher.

  • Things to do
  • Gold Coast

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.

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  • Things to do
  • Lincoln Square

Make your Halloween a little BOO-zier (get it?) during the Ravenswood Costume Crawl, which invites costumed attendees to stroll along a route stocked with local desserts, snacks and beer and cocktail samples on Montrose Avenue. Check-in is at Teddy's Ice Cream, and tickets include eight tasting portions. The three best dressed will win prizes from KOVAL Distillery.

  • Things to do
  • West Loop

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.

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  • Things to do
  • River North

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.

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  • Nightlife
  • Loop

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. 

  • Bars
  • Lower West Side

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.

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  • Things to do
  • Quirky events
  • Streeterville

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! 

  • Nightlife
  • Nightlife
  • Loop

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.

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  • Theater
  • Interactive
  • Lake View

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.

  • Things to do
  • Festivals
  • Lake View

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.

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  • Things to do
  • River West/West Town

Frontier will offer an all-you-can-eat spread of sausages, pretzels and sides during its Oktoberfest party on October 14. Each $35 ticket includes one beer in a complimentary stein; Oktoberfest drafts are $6. Guests can also win prizes in a stein-holding contest.

  • Things to do
  • Loop

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.

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  • Things to do
  • West Loop

Put on your best pink attire and let your nostalgia run wild at this pop-up inspired by the iconic doll. Fans will enjoy all-day brunch fare from Master Chef semi-finalist Becky Brown and sip on refreshing cocktails while hanging out on a breezy, beach-themed patio. There are plenty of photo ops—including a life-sized Barbie box—plus exclusive merch to pick up. You can even strap on roller skates and glide around an outdoor rink!

  • Kids
  • Old Town

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.

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  • Museums
  • Museum Campus

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.

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  • Things to do
  • Logan Square

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.

  • Art
  • Film and video

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.

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  • Shopping
  • Markets and fairs
  • West Loop

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.

GYG Chicago TTD

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