October 2018 events calendar for Chicago

Plot out your October in Chicago with our calendar of things to do, including the best theater and concerts
Arts in the Dark
Photograph: Courtesy Arts in the Dark
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The spookiest month of the year is officially upon us, packed with events that will make you feel lucky that you're in Chicago. Make a sign and cheer on tireless runners along the Chicago Marathon's sprawling 26.2-mile route. Get a new perspective while touring the interiors of some of the city's most beautiful buildings during Open House Chicago. Of course, you'll want to put on a costume and close out October with some frightening Halloween festivities.

RECOMMENDED: Events calendar for Chicago in 2018

Featured events in October 2018

Jack o Lantern
Photograph: Pixabay
Things to do, Festivals

Jack's Pumpkin Nights

icon-location-pin River West/West Town
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Want to run through a corn maze without making a trip to the suburbs? Jack's Pumpkin Nights, a new Halloween-themed pop-up experience, brings the seasonal outdoor fun to a two-acre lot near Goose Island. Guests can enjoy pumpkin carving, carnival games and nightly live performances from sword swallowers and fire dancers. Plus, there's a bar inside of the corn maze stocked with beer and cider. 

Christine McVie returns to the stage with Fleetwood Mac at a packed Allstate Arena on Feb 14, 2015.
Photograph: Joshua Mellin
Music, Rock and indie

Fleetwood Mac

icon-location-pin United Center
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Just when we thought that the classic, Rumours-era lineup of Fleetwood Mac was back together for good, the group recently announced that founding member Lindsey Buckingham was kicked out of the band. He'll be replaced on tour by Tom Petty guitarist Mike Campbell and Crowded House frontman Neil Finn—two experienced musicians who certainly know their way around tracks like “Gold Dust Woman” and “Tusk.”  Of course, Stevie Nicks, Mick Fleetwood, John McVie and Christine McVie are still in the group, so hopefully their soaring vocal harmonies are enough to cover up Buckingham's conspicuous absence. 

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Things to do, Festivals

Lincoln Square Apple Fest

icon-location-pin Lincoln Square
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Kick off autumn with hot apple cider, freshly baked apple pie and a variety of other apple-based goods at this annual Lincoln Square festival where Giddings Plaza transforms into an urban apple orchard. Let your kids loose in the Kid Zone while sipping hard cider then keep the apple love going and take home your own bushel.

Beer
Photograph: Shutterstock
Things to do, Festivals

Far & Away

icon-location-pin Millennium Park
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Looking for beers that you can almost never find on tap in Chicago? Half Acre's new Far & Away event gathers some of the nation's top breweries—including Fremont, Jackie O's, Jester King and Mikkeller—for two sessions of tasting atop the Harris Theater Rooftop Terrace. In addition to trying sought-after beers, you'll also be supporting a great cause—a portion of proceeds from the event support the Intonation Music Workshop, which provides music education for Chicago youth.

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Things to do, Festivals

Chicago Rare and Wild Beer Fest

icon-location-pin Museum Campus
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Barrel ages, funky and sour beers take the spotlight at this annual festival, which takes place in the Field Museum's Stanley Field Hall. You'll find rare and sought-after selections from the likes of Hopewell, Noon Whistle, Surly and more than 60 other breweries in attenance at the festival. Each ticket includes 50 tasting vouchers, which you can use to sample any of the beers being poured. 

Things to do

Yoga on the Lake

icon-location-pin Lincoln Park
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Wake up and get down (dog) at Yoga on the Lake presented by Bloody Mary Fest. Before the festival begins, roll out a mat at Theater on the Lake and participate in a 60-minute vinyasa flow lead by Yoga Squad. After breaking a sweat at the morning workout, guests can sip brunch cocktails and munch on breakfast tacos from Pink Taco. Of course, you can also spring for an all-day ticket and stick around for the Bloody Mary competition, which begins at noon. 

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Things to do, Festivals

Bloody Mary Fest

icon-location-pin Lincoln Park
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Do Sunday Funday right with Chicago Sport & Social’s annual Bloody Mary battle. Hosted at Theater on the Lake, the event features savory brunch cocktails from some of Chicago's top restaurants and bars. Guests are invited to taste their way through the lineup and vote for a winner. In addition to Bloodys, enjoy brunch bites, two full drinks, live music, lawn games and an artisan market. VIP ticket holders get express entry, access to a private seating area, an extra full-size drink and a festival souvenir.

Gorillaz
Illustration: Jamie Hewlett
Music, Rap, hip-hop and R&B

Gorillaz + The Internet

icon-location-pin United Center
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Last summer, Damon Albarn and his cartoon band threw a house music dance party on the shores of Lake Michigan when Gorillaz kicked off its North American tour in Chicago. A little more than a year later, the group has a new album, The Now Now, which functions as a solo record by animated Gorillaz frontman 2D. The group's latest electro-pop ballads don't quite live up to the cosmic funk that Albarn explored on Humanz, but the project's new arena show should be as thrilling as ever—expect sing-along renditions of "Clint Eastwood" and " Stylo" as well as apperances from a few special guests (Vince Staples, Jamie Principle and Del the Funky Homosapien showed up in Chicago last summer). Los Angeles neo-soul outfit the Internet open the show.

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Shopping

Randolph Street Market Festival

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More than 200 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

Arts in the Dark
Photograph: Courtesy Arts in the Dark
Things to do, Festivals

Arts in the Dark

icon-location-pin Loop
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Celebrate Halloween a few days early at the Arts in the Dark parade, which sends a string of performers, puppets, lanterns and floats through the streets of Chicago. Local artists help create most of the costumes and objects featured in the parade, making this annual tradition a celebration of local creativity (as well as spooky sights). This year, the procession moves from Grant Park to State Street, where it will begin at Lake Street and move south to Van Buren. 

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Nine Inch Nails deliver an industrial set in Grant Park at Lollapalooza Music Festival 2013 on Friday, August 2.
Photograph: cousindaniel.com
Music, Rock and indie

Nine Inch Nails + The Jesus and Mary Chain

icon-location-pin Uptown
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Ever since reviving Nine Inch Nails in 2013, Trent Reznor and Atticus Ross have made a point of pushing the group forward rather than dwelling on the past. How else do you explain the nearly relentless stream of albums and EPs, each exploring a slightly different strain of NIN's industrial alt-rock sound. That's not to say that the pair have put the past behind them—NIN's headlining set at Riot Fest in 2017 felt like an encapsulation of the group's best work, buoyed by years of experience and a fanbase that's willing to let Reznor indulge in whatever he likes. Expect to hear some David Bowie-inspired tunes from the latest NIN album, Bad Witch, during the band's three-night stand at the Aragon Ballroom.

Kids

Spooky Zoo

icon-location-pin Lincoln Park
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This fun and free alternative to trick-or-treating attracts more than 30,000 kiddos and their families to the zoo each year. The fall-filled festival features Ferris wheel rides, a corn maze, animal-enrichment activities, live entertainment and a pumpkin carver. Come in costume and prepare to have a ghoulish good time! 

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Tom Hanks
Photograph: Courtesy Chicago Humanities Festival
Things to do, Festivals

Chicago Humanities Festival: Graphic!

icon-location-pin Loop
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Devoted to making the humanities a vibrant and exciting part of everyday life, this ambitious event brings together some of the world's best and brightest individuals to celebrate human creativity. The theme the Chicago Humanities Festival's fall lineup is “Graphic!,” exploring the various facets of visual culture as well as the ways in which it is rapidly evolving. Among this year's slate of guests are Academy Award-winning actor Tom Hanks, Broad City co-creator and star Abbi Jacobson, Two Dope Queens co-creator and podcast host Phoebe Robinson, Getty Images photographer John Moore and comic book artist Alex Ross. You can find a complete list of Chicago Humanities Festival panels and discussions on its official website.

Concerts in October 2018

Sting & Shaggy
Photograph: Courtesy the artist
Music, Reggae and dancehall

Sting + Shaggy

icon-location-pin Uptown
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English rocker-turned-adult contemporary mainstay Sting has been known to tour with Peter Gabriel, but his latest jaunt through North America pairs him with Jamaican singer Shaggy, best known for his 2000 single about banging on the bathroom floor. The duo released an album of reggae-tinged songs earlier this year, but we're far more excited to hear what Shaggy can add to “Every Breath You Take” and “Message in a Bottle,” as well as Sting's shouted refrains on “It Wasn't Me.” 

Ed Sheeran
Photographer: Dan Curwin
Music, Pop

Ed Sheeran + Snow Patrol + Lauv

icon-location-pin Museum Campus
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Even if you didn't catch his controversial cameo on Game of Thrones, you've surely heard "Shape of You" blasting from a car at least a hundred times this year. Taylor Swift's good friend Ed Sheeran is still winning (adolescent) hearts and minds, so of course he's also headlining Soldier Field Stadium. 

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Eleanor Friedberger
Photograph: Chris Eckert
Music, Rock and indie

Eleanor Friedberger + Pill

icon-location-pin Ukrainian Village
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While Chicago über-indie darlings the Fiery Furnaces sustain their not-necessarily-broken-up hiatus, Eleanor Friedberger carries on with her latest solo album. Rebound!, her fourth record, was inspired by an ‘80s goth disco that Friedberger visited while spending time in Greece, where much of her extended family lives. The resulting album maintains the jaunty feel of her previous output, augmented by drum machines and synthesizer melodies—it's the sunniest interpretation of goth electronica that we've ever heard. Experimental New York punk outfit Pill opens the show.

Justin Timberlake
Photograph: Courtesy RCA Records
Music, Pop

Justin Timberlake

icon-location-pin United Center
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While a rough Super Bowl appearance and the questionable roll-out of his latest album weren't great looks for J.T., the pop superstar's swagger and charisma have gotten him through worse scrapes. For better or for worse, Man of the Woods is more of what Timberlake does best, combining taut pop production with nods to funk, electronica and country. The merch stand will probably look like a Pendleton catalog and you'll probably be subjected to that camo-deer suit jacket again, but that's price you'll have to pay to hear "SexyBack" live.

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The Revolution
Photograph: Courtesy the artist
Music, Funk, soul and disco

The Revolution

icon-location-pin Lincoln Park
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Best known as the backing band for Prince's Purple Rain, the Revolution was the funky, multi-cultural backbone of some of the Minneapolis artist's most seminal work. Though the group disbanded in the ‘80s, some of its founding members (including guitarist Wendy Melvoin and drummer Bobby Z) reunited in the wake of Prince's sudden death in 2016. Here, they'll celebrate the life of their late collaborator with a tribute to the Purple One's revolutionary spirit and sound.

Christine McVie returns to the stage with Fleetwood Mac at a packed Allstate Arena on Feb 14, 2015.
Photograph: Joshua Mellin
Music, Rock and indie

Fleetwood Mac

icon-location-pin United Center
icon-calendar

Just when we thought that the classic, Rumours-era lineup of Fleetwood Mac was back together for good, the group recently announced that founding member Lindsey Buckingham was kicked out of the band. He'll be replaced on tour by Tom Petty guitarist Mike Campbell and Crowded House frontman Neil Finn—two experienced musicians who certainly know their way around tracks like “Gold Dust Woman” and “Tusk.”  Of course, Stevie Nicks, Mick Fleetwood, John McVie and Christine McVie are still in the group, so hopefully their soaring vocal harmonies are enough to cover up Buckingham's conspicuous absence. 

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Music, Rock and indie

Death Cab for Cutie + Charly Bliss

icon-location-pin Loop
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Ben Gibbard and his band are indie-rock survivors, capitalizing on the genre's The O.C.-soundtracking days and managing to bring its earnest refrains and scrappy pop sensibility  into the latter hald the 2010s relatively unscathed. Death Cab for Cutie's latest album, Thank You For Today, is stuck somewhere between electronics-heavy homages to Gibbard's days in the Postal Service and songs that introduce a high-fidelity sheen to the sound of the band's earliest records. At this special theater gig, you'll be able to embrace the Death Cab's latest work and acknowledge the past with an obligatory “Soul Meets Body” sing-along.

Gorillaz
Illustration: Jamie Hewlett
Music, Rap, hip-hop and R&B

Gorillaz + The Internet

icon-location-pin United Center
icon-calendar

Last summer, Damon Albarn and his cartoon band threw a house music dance party on the shores of Lake Michigan when Gorillaz kicked off its North American tour in Chicago. A little more than a year later, the group has a new album, The Now Now, which functions as a solo record by animated Gorillaz frontman 2D. The group's latest electro-pop ballads don't quite live up to the cosmic funk that Albarn explored on Humanz, but the project's new arena show should be as thrilling as ever—expect sing-along renditions of "Clint Eastwood" and " Stylo" as well as apperances from a few special guests (Vince Staples, Jamie Principle and Del the Funky Homosapien showed up in Chicago last summer). Los Angeles neo-soul outfit the Internet open the show.

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Christina Aguilera
Photograph: Luke Gilford
Music, Pop

Christina Aguilera

icon-location-pin Loop
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Like every other early-aughts pop starlet, Christina Aguilera has struggled to find her place in the modern pop landscape, trying her hand at acting and becoming a vocal coach on the TV series The Voice. Aguilera's powerful, versatile voice has always been her biggest asset, so it's no surprise that the singing on her new album, Liberation, is amazing, even when her song and production choices falter. If you can look past ill-conceived forays into trap and R&B (including the lackluster Kanye West-produced single “Accelerate”), you can look forward to hearing some unabashed pop anthems alongside classics like “Genie in a Bottle” and “Beautiful.”

Twenty One Pilots
Photograph: Jabari Jacobs
Music, Rock and indie

Twenty One Pilots

icon-location-pin United Center
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Combining reggae, rap-rock and a bit of ukulele balladry, Columbus, Ohio duo Twenty One Pilots has become one of the hottest new pop acts—the kind that accepts Grammy awards in its underwear. On the heels of the pair's new album TRENCH, the unlikey Top 40 juggeranuts will return to the United Center, and you better believe that it's going to be completely sold out.

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