October 2018 events calendar for Chicago

Plan your October in Chicago with our events calendar of the best activities, including free things to do, and picks from theater, art and music
Photograph: Matthew Sperzel
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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

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.

Concerts in October 2018

Deerhoof
Photograph: Courtesy the artist
Music, Rock and indie

Deerhoof + Sad13 + Lily and Horn Horse

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Endlessly catchy and boundlessly energetic, Deerhoof's two-plus decades of musical output is still full of surprises. The quartet's latest album, Mountain Moves, find the group collaborating with artists like Lætitia Sadier and Xenia Rubinos, providing a contrast to the chirpy vocals of lead singer Satomi Matsuzaki and the band's blistering funk-punk arrangements. Here, Deerhoof squeezes back into the Empty Bottle in celebration of the venue's 25th anniversary, joined by Speedy Ortiz singer Sadie Dupuis (under her Sad13 moniker) and effervecent synth-pop duo Lily and Horn Horse.

Holy Fuck
Photograph: Nick Walker
Music, Dance and electronic

Holy Fuck

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While James Murphy and all his friends embrace a glitzy, nostalgic take on dance rock, Canadian collective Holy Fuck finds the genre's sinister edge. The songs that populate the group's 2016 album Congrats combine menacing rhythms with foreboding waves of distortion, lending post-punk energy to the upbeat tempos. Here, the group sets up in the middle of Thalia Hall's floor for one of the venue's signature "in the round" performances, which should allow plenty of space for you to show off your most aggressive dance moves.

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Explosions in the Sky
Photograph: Nick Simonite
Music, Rock and indie

Explosions in the Sky

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If you've ever watched an episode of Friday Night Lights, you've probably heard the triumphant, guitar-driven strains of Explosions in the Sky. The Texas post-rock outfit has been mining grandiose, soundtrack-worthy melodies and slowly building arrangements for more than 15 years. One of the band's first gigs took place on the Empty Bottle's stage, so it's fitting that Explosions is returning to celebrate the venue's 25th anniversary.

Music, Folk, country and blues

Fleet Foxes

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No longer saddled with the status of folk rock poster boy, folk rocker Robin Pecknold gets downright introspective on Crack-Up. Returning to Fleet Foxes after a brief stint in college, Pecknold treats his third LP like a thesis, constructing intricate suites of songs that allow him ample room to tackle weighty themes and confront the momentous changes in his life. While it lacks the immediacy of Fleet Foxes past work, it's all the more impressive for its lofty ambitions.

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Future Islands at Pitchfork Music Festival
Photograph: cousindaniel.com
Music, Rock and indie

Future Islands + Jenny Besetzt

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If you fell in love with Future Islands' romantic electro-pop and the meme-worthy dance moves of frontman Samuel T. Herring through the group's 2014 release, Singles, you're probably going to dig its latest album. Seasons may change, but the Baltimore outfit's new LP, The Far Field, opts for more of the same, featuring plenty of pleasant synth melodies and Herring's earnest vocal delivery. At this special show celebrating the 25th anniversary of the Empty Bottle, the band is joined by dark indie pop band Jenny Besetzt.

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Courtesy of: Windish Agency
Music, Dance and electronic

Four Tet (DJ set)

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Under the moniker of Four Tet, Kieran Hebden blends jazz, rock and electronic, in addition to remixing tracks by the likes of Radiohead, Sia and the xx. You can expect his eclectic tastes to be on display as he takes over the decks at Smart Bar for an all-night DJ set, in honor of the venue's 35th anniversary. 

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Music, Rock and indie

Hanson

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Yep, it's already been 20 years since "MMMBop" introduced us to the trio of kids with the shaggy haircuts and irresistible pop harmonies. Now the Hanson boys are all grown up, have started a brewery and are celebrating the 25th anniversary of the band on its Middle of Everywhere tour. Get ready for an evening of perky power pop and a couple pints of the Hanson Brothers Beer Co.'s MMMHops Pale Ale.

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Photograph: Michael Halsband
Music, Rock and indie

Pixies + Mitski

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The Pixies could easily be a nostalgia act at this point in its career, cashing in on the anniversaries of albums like Surfer Rosa and Doolittle or the mere presence of "Where is my Mind" on the Fight Club soundtrack. Instead, frontman Black Francis continues to treat the reunited group like his primary creative outlet—not even the departure of longtime bassist Kim Deal has dampened his spirits. On the latest Pixies album, Head Carrier, Francis departs from the loud-soft dynamic template he employed on the group's best records, opting for a punk rock assault that lacks any subtlety. It might be a difficult change to stomach for longtime fans, but there's little doubt that you'll hear "Here Comes Your Man" if you you tough it out. Indie rock singer-songwriter Mitski opens the show.

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Iron & Wine
Photograph: Kim Black
Music, Folk, country and blues

Iron & Wine

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It's been more than since Florida folk singer Sam Beam recorded a cover of the Postal Service's "Such Great Heights" that was nearly inescapable for a few years. After a few records that ditched the  restrained and hushed songcraft of Beam's original records, the latest Iron and Wine album, Beast Epic, smartly dials back the studio gloss and focuses on captivating lyricism. Listen closely, and you'll hear Beam grapple with the ceasless march of time as well as the joys and indignities of aging. On October 12, local trio Ohmme opens the show, while alt-country singer-songwriter John Moreland supports of October 13.

Music, Punk and metal

Pelican + Grails + Jaye Jayle

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Chicago-based instrumental metal act Pelican returns to the Empty Bottle's stage to mark the venue's 25th anniversary. The band hasn't released a studio album since 2013's Forever Becoming, but the group's members have remainder busy with side projects in the interim. If the creative juices are flowing, perhaps you'll hear a couple of new, floor-shaking tunes. Experimental rockers Grails and eerie folk rocker Jaye Jayle open the show.

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Comedy in October 2018

Photograph: Byron Hatfield
Comedy, Sketch shows

Bye Bye Liver: The Chicago Drinking Play

icon-location-pin Lake View
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"Bye Bye Liver" combines two robust Chicago traditions: comedy and heavy drinking. The show opened ten years ago for a three-week run, then kept getting extended. It centers on common party situations most Chicagoans can relate to, and incoroprates interactive audience games like "Would You Rather." If you're looking to get drunk, quick, and have a great time doing so, "Bye Bye Liver" is always a solid bet. 

iO Theater
Photograph: Anthony Soave
Comedy, Improv

Whirled News Tonight

icon-location-pin River North
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 Now in its 15th year, Whirled News Tonight has become an institution at the iO Theatre, hence its prime time slot. Improvised scenes are based on news articles from that week, which audience members post to the back wall of the stage. The show boasts alumni including Jordan Klepper (The Daily Show, The Opposition with Jordan Klepper), Sarah Haskins (Trophy Wife), Arnie Niekamp (Hello From the Magic Tavern) and more. 

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Comedians You Should Know
Photograph: Melissa Mamroth
Comedy, Stand-up

Comedians You Should Know

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This weekly night of comedy, curated by a group of funny dudes, puts local stand-ups on your radar. It's totally free and BYOB, so why not?

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