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October 2019 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 2018, halloween parade
Photograph: Neal O'Bryan
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Fall in Chicago is in full swing, and October's event calendar is filled with some of the biggest events of the year, including the annual Chicago Marathon and the Chicago International Film Festival. When you're not cheering on runners or watching an exciting flick, you can see famous folks in conversation during Chicago Ideas Week, witness a creative parade down State Street at Arts in the Dark or dress up to attend a Chicago Halloween party. Plus, the Lyric Opera's new season has begun, a gigantic Andy Warhol exhibition is opening at the Art Institute and Madonna is headlining a seven-night stand at the Chicago Theatre. Find the best things to do in Chicago this month on our October events calendar.

RECOMMENDED: Events calendar for Chicago in 2019

Featured events in October 2019

Photograph: Courtesy Lincoln Park Zoo
Kids

Fall Fest at Lincoln Park Zoo

icon-location-pin Lincoln Park Zoo | Chicago, IL, Lincoln Park
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Get your fall feels on at this free festival that begins at the tail end of September. You can snag a photo with a giant pumpkin, watch master carvers at work, explore an edible garden, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences ($3 per ticket, $27 for 10, $51 for 20) such as caousel rides, a bounce house, a Ferris wheel, corn mazes, a slide and an obstacle course. Take a look at the Lincoln Park Zoo's webite for a complete list of activites and events throughout Fall Fest.

Jack's Pumpkin Pop-up
Photograph: Courtesy Jack's Pumpkin Pop-up
Things to do, Festivals

Jack's Pumpkin Pop-up

icon-location-pin 1265 W Le Moyne St, River West/West Town
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Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpking Pop-up saves you a trip to the suburbs by bringing a corn maze, thousands of pumpkins and an array of carnival games to the city. This year's edition of the outdoor event features a larger corn maze that contains a hidden bar, a "gypsy caravan" as well as plenty of photo backdrops and props (think tractors, trucks and piles of pumpkins) for you to take advantage of. Plus, the pop-up will also host events throughout its four-week run, including a pumpkin walk, a beer and cider festival and a sweet corn festival.

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Jack o lantern
Photograph: David Menidrey on Unsplash
Things to do, Exhibitions

Pier Pumpkin Lights

icon-location-pin Navy Pier | Chicago, IL, Streeterville
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You'll find nearly 1,000 glowing pumpkins spread across Navy Pier at the attraction's month-long Pier Pumpkin Lights event. Stop by Polk Bros Park to visit the Juggernaut of Jack-O-Lanterns installation then head to the pier to take in five more pop-up experiences, all of which will be illuminated after dusk each evening. Navy Pier restaurants such as Bubba Gump Shrimp Co, Tiny Tavern and Snow Dragon Shavery will be offering food and drink specials throughout the month of October, and Amazing Chicago’s Funhouse Maze will transform into a haunted maze on select weekends. Plus, you can bring the kids to trick-or-treat at Navy Pier on October 26, 27 and 31.

Apichatpong Weerasethakul, Ghost Teen 2009
Photograph: Courtesy FarEastFarWest
Art, Photography

“Third Realm”

icon-location-pin Museum of Contemporary Photography, Loop
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The Shanghai-based FarEastFarWest collection curates a selection of images taken by artists from China, Thailand, the Philippines, Japan, Korea and Indonesia between 2007 and 2013— a particularly fertile period for Asian photography. The exhibition takes its name from the artists' practice of using photos to investigate the spaces in-between various concepts, whether its the past and the present or a local perspective and a global view.

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Begyle Brewing Company
Photograph: Laura Rote
Things to do, Festivals

Oktoberfestiversary

Dovetail Brewery and Begyle Brewing team up for another outdoor bash in their shared parking lot, stocked with live music, food trucks and plenty of beer. DönerMen, Three Legged Tacos, Bopbartruck, Pualina Meat Market and more local eateries will be serving dishes throughout the two-day fest, accompanied by a selection of seasonal suds from each of the breweries. Plus, kids can get an inflatable creation from a balloon artist, you can try your hand at a game of skee ball and Luckyprints will be on-hand printing on-demand shirts. Proceeds from the event benefit the Friendship Center food pantries.

Things to do, Festivals

Chicago Ideas Week

icon-location-pin Various locations throughout Chicago,
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Learn more about politics, technology, cannabis, creativity, leadership and other interesting topics at the latest edition of Chicago Ideas Week. The week-long event brings together hundreds of thought leaders representing a variety of fields for a series of discussions and panels that take place in front of a live audience. Plus, attendees can also take part in a series of lab experiences, where you can take a yoga class surrounded by bunnies, visit the Cinespace Chicago Film Studios or learn about screenprinting from streetwear pros. This year's Chicago Ideas Week lineup includes former U.S. Secretary of State Hillary Clinton, author Chelsea Clinton, director David Lynch, actress Jessica Lange, musician Liz Phair and comedian Pete Holmes. Discussions will revolve around topics like the state of the world in 2050, journalism in the age of disinformation and the rise of artificial intelligence. If you're looking for inspiration or enlightenment, this is the place to be.

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Photo: Claire Folger/Lionsgate
Movies

Chicago International Film Festival

icon-location-pin AMC River East 21, Streeterville
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Film buffs get a chance to see the hottest movies on the festival circuit at the Chicago International Film Festival, which presents a lineup of dramas, documentaries, comedies, foreign films and more. The screenings take place at AMC River East 21, where you can see Edward Norton's period detective drama Motherless Brooklyn open the festival. Other highlights of the 2019 lineup include special presentations of Rian Johnson's (Star Wars: The Last Jedi) murder mystery Knives Out, Terrence Malick's World War II-era drama A Hidden Life and Taika Waititi's biting World War II satire Jojo Rabbit.

arts in the dark 2018, halloween parade
Photograph: Neal O'Bryan
Things to do, Festivals

Arts in the Dark

icon-location-pin State St and Lake St, Loop
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Celebrate Halloween a few days early at the Arts in the Dark parade, which sends performers, puppets, bands, lanterns and floats through the streets of Chicago. Local artists construct most of the costumes and objects featured in the parade, making this annual tradition a celebration of local creativity (as well as spooky sights). The procession begins at State Street and Lake Street and moves south to Van Buren.

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The vintage facade of the Music Box makes it one of the best movie theaters in Chicago.
Photograph: Max Herman
Movies, Horror

Music Box of Horrors

icon-location-pin Music Box Theatre, Wrigleyville
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Bring a seat cushion and settle in for a 24-hour marathon of frightening, thrilling and chilling movies at the Music Box Theatre. Ticketholders will be able to catch screenings of the 2002 Sci-Fi Channel movie Dog Soldiers, 1928 silent movie The Man Who Laughs (accompanied by a live organ score), Halloween IIThe Fly II and the original Buffy The Vampire Slayer film. Plus, you'll be able to shop for eerie items provider by vendors like Bric-a-Brac Records, Creepy Co., Graveface Records and Deadly Prey Gallery while enjoying grub from the Empanada Bike, Cheesie's and Taco in a Bag.

St. Jerome, Open House Chicago
Photograph: Eric Allix Rogers
Things to do, Festivals

Open House Chicago

icon-location-pin Various locations throughout Chicago,
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Want to take a look inside skyscrapers, private clubs, churches, theaters and historic homes throughout the city? The Chicago Architecture Center annual Open House Chicago event offers a behind-the-scenes look at more than 350 buildings spread across 38 neighborhoods—and it's all absolutely free. This year's lineup of sites adds locations in Irving Park, Portage Park and Jefferson Park, such as the Copernicus Center, Carl Schurz High School and the Irish American Heritage Center. In honor of the Year of Chicago Theater, you'll also be able to step into performance spaces such as the James M. Nederlander Theatre, the Second City and University of Chicago's new Green Line Performing Arts Center. All tours are first-come, first-served, so plot out your list and prepare to explore Chicago all weekend long.

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Andy Warhol. Skull, 1976.
Photograph: © 2019 The Andy Warhol Foundation for the Visual Arts, Inc. / Artists Rights Society (ARS), New York.
Art, Contemporary art

“Andy Warhol—From A to B and Back Again”

icon-location-pin Art Institute of Chicago | Chicago, IL, Grant Park
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Arriving in the midwest after drawing hordes in San Francisco and New York, this retrospective (the first to be organized by a U.S. institution since 1989) of Andy Warhol's career features more than 350 works for guests to explore. Instead of focusing on a specific era of his life, “From A to B and Back Again” accounts for the entire breadth of the Pop Art legend's output, from early illustrations that were commissioned for magazines to recolored portraits of celebrities that graced the cover of Interview magazine. While there are plenty of familiar pieces on display (a print of Marilyn Monroe, several Campbell's soup cans), there are also sections of the exhibit devoted to lesser-known aspects of Warhol's practice, including performance art, television and publishing. Filled with self-portraits, homages to vaunted brands and celebrations of fame, “From A to B and Back Again” accentuates the echoes of Warhol’s art in the contemporary world—and seeing so much of it one place only makes its prophetic themes that much clearer.

Bloody Mary
Photograph: Unsplash
Things to do, Festivals

Bloody Mary Fest

icon-location-pin Theater on the Lake, Lincoln Park
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The most ubiquitous breakfast cocktail gets its very own festival at Theatre on the Lake, where attendees can choose from two sessions of drinks, brunch bites, games and live music as some of the city’s top bartenders try to concoct the most creative Bloody Mary interpretation. You'll find drinks overflowing with toppings, lawn games to enjoy, an artisan market to shop at and optional yoga or three-mile run ticket add-ons.

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Photograph: Courtesy Gallagher Way
Things to do, Festivals

Pumpkin Party at Gallagher Way

icon-location-pin Gallagher Way, Wrigleyville
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Bring the kids to Gallagher Way for an early Halloween celebration in Wrigleyville, where costumed attendees can trick-or-treat around the park and participate in a variety of activities. You'll be able to listen to tunes supplied by the Old Town School of Folk Music, create a clay Halloween character with the help of Kid Create Studio and snag treats from Garrett Popcorn or Fannie May. Stick around to catch an outdoor screening of Hocus Pocus on Gallagher Way's video screen, beginning at 5:30pm.

Hallie Duesenberg
Shopping

Randolph Street Market Festival

icon-location-pin Randolph Street Market, West Loop
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More than 100 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. In October, most of the market moves indoors to the Chicago’s Plumbers Hall, so there's no need to worry about shopping in the chilly autumn air.

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Photograph: Fox and Harrison Photography
Things to do, Late openings

Lyric Halloween Masquerade

icon-location-pin Civic Opera House | Chicago, IL, Loop
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Spend a haunted evening in the Civic Opera House at the Lyric Halloween Masquerade, which raises money to support emerging operatic talent. Attendees are encouraged to arrive dressed in a mask and formal attire (or their favorite Halloween costume) for a party that includes cocktails, beer, bites from local restaurants and a live DJ.

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Concerts in October 2019

Mucca Pazza
Photograph: Jason Creps
Music, Rock and indie

Mucca Pazza

icon-location-pin Hideout, River West/West Town
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Local weirdo marching band Mucca Pazza brings its mismatched uniforms, horns, cellists, guitarists, drummers and enthusiastic cheerleaders to the Hideout during the month of October for a weekly residency. Every show promises to be a bit different than the last, with dancers, puppeteers and singers joining the expansive collective as it explores everything from Balkan music to big band arrangements. Frankly, we're just curious to see how Mucca Pazza manages to squeeze its 30-odd members and an audience into the Hideout's cozy confines.

Pitchfork Music Festival, Jay Som
Photograph: Carolina Rodriguez
Music, Rock and indie

Jay Som + Gia Margaret + Boy Scouts

icon-location-pin Lincoln Hall, Sheffield & DePaul
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Written during a week-long stay at Joshua Tree National Park, Anak Ko (“my child" in Tagalog, a native dialect of the Philippines) finds Melina Duterte looking inward and finding ways to embrace seismic changes in her life—sobreity, a move to Los Angeles and success. Recorded in her home studio with the help of some friends, the latest Jay Som album channels the same dreamy vibes as Duterte's previous doses of bedroom pop but feels more comfortable exploring new territory. From a jazzy tune about the pitfalls of social media ("Tenderness") to a twangy ballad about getting sober ("Get Well"), some of the album's most arresting moments come when Duterte comes out for behind the wall of fuzzed-out guitars. At Lincoln Hall, Jay Som is joined by local singer-songwriter Gia Margaret and Oakland indie-folk act Boy Scouts.

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Jidenna
Photograph: Munachi Osegbu, Courtesy Epic Records
Music, Rap, hip-hop and R&B

Jidenna

icon-location-pin House of Blues, River North
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Dapper "Classic Man" singer Jidenna met Janelle Monáe at masquerade party, impressing her so much that she subsequently signed him to her Wondaland Record imprint, which released his debut album, The Chief. The singer-songwriter's sophomore record, 85 to Africa, explores the African dispora through tunes that augment contemporary hip-hop and R&B production with afropop rhythms and dancehall beats (which have already infiltrated the sonic palette of countless mainstream pop artists). Even if the music Jidenna is making isn't entirely groundbreaking, he boasts an undeniable earnestness and swagger that escapes most performers—especially when he inevitably dons a smart suit for a performance of his most well-known single.

Sleater-Kinney
Photograph: Nikko LaMere
Music, Rock and indie

Sleater-Kinney + Shamir

icon-location-pin Riviera Theatre, Uptown
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Sleater-Kinney's reunion in 2015 was a welcome and needed comeback, but the group has weathered some major changes in the wake of its second album since the band's return. Enlisting Annie Clark (a.k.a. St. Vincent) to handle production duties, The Center Won't Hold takes Sleater-Kinney into the realm of pop music, adding prominent bass lines and synth melodies to a collection of urgent anthems. Though the album was recorded as a trio, Carrie Brownstein and Corin Tucker will take the stage without longtime drummer Janet Weiss—she announced her departure from the group in July, stating "it is time for me to move on." During its two-night stand at the Riviera, Sleater-Kinney is joined by singer-songwriter Shamir, who has left behind the bouyant pop of his debut album Rachet in favor of country-inflected indie-rock.

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Tobacco
Photograph: Maureen Boyle
Music, Dance and electronic

Ghostly 20: Tobacco + Shigeto + Drama + Steve Hauschildt + SV4

icon-location-pin Metro Chicago, Wrigleyville
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Brooklyn-based electronic record label Ghostly International marks its 20th anniversary with a showcase at Metro, featuring a selection of artists from its roster. Black Moth Super Rainbow frontman and woozy vocoder-laden synth-pop aficionado Tobacco headlines the evening, joined by the jazz-inflected beat-maker Shigeto, electro-pop duo Drama, minimalist techno artist Steve Hauschildt and Ghostly International founder Sam Valenti (a.k.a. SV4).

Sigur Ros | Lollapalooza | August 5, 2012
Photograph: Ryan Bourque
Music, Classical and opera

Jónsi & Alex Somers

icon-location-pin Copernicus Center, Jefferson Park
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Sigur Rós frontman Jónsi and his partner Alex Somers celebrate the 10th anniversary of their collaborative album, Riceboy Sleeps, by presenting the first-ever live performances of the record in its entirety, accompanied by an orchestra and a choir. The tracks contained on the ambient album sound like the bits between your faviorite Sigur Rós songs, stretched out into expansive compositions that wrap layers of vocals and strings around subtle textural noises, like rustling wind and tinkling glass. Settle in for a meditative evening filled with understated sounds and swelling crescendos—you can probably leave your earplugs at home.

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Young Thug
Photograph: Garrett Coyte, Courtesy Atlantic Records
Music, Rap, hip-hop and R&B

Young Thug + Machine Gun Kelly

icon-location-pin Credit Union 1 Arena at UIC, Little Italy, UIC
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Though Young Thug may be best known for his Auto-Tuned verses on tracks by the likes of Camila Cabello and Post Malone, it's his unpredictable marble-mouthed delivery and improvised lyrics that make him one of hip-hop's most interesting and frequently imitated personalities. His debut album (he classifies everything he's released up to now as a "mixtape") So Much Fun plays to Thugger's strengths, letting him string stream-of-conscious rhymes together atop inoffensive trap beats while trading verses with collaborators like Future, Gunna and Lil Baby. During his stop at the Credit Union 1 Arena, Young Thug is joined by rap-rocker Machine Gun Kelly.

Madonna brought her Rebel Heart tour to the United Center on September 28, 2015.
Photograph: Chris Sullivan
Music, Pop

Madonna

icon-location-pin Chicago Theatre | Chicago, IL, Loop
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Madame X, the 14th studio album from Madonna, casts the 60-year-old Queen of Pop as a secret agent, taking on different guises and identities as she travels across the world—a concept that will undoubtedly serve as an excuse for a cavalcade of costume changes during live performances. Crafted in the wake of Madge's recent move to Lisbon, Portugal, her latest record oozes with the trendy sounds of Latin pop, including the sultry lead single "Medellín" featuring Columbian singer Maluma. Collaborations with rappers Quavo and Swae Lee suggest that Madonna will also be dabbling in some trap-tinged tunes, which seem destined to rank among her most desperate attempts at cultural relevance (remember the EDM bangers from her last few records?). Thank goodness that she has multiple decades worth of classic pop songs to fall back on.

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JPEGMAFIA
Photograph: Alec Marchant
Music, Rap, hip-hop and R&B

JPEGMAFIA + Butch Dawson

icon-location-pin Bottom Lounge, West Loop
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The frantic, energetic presence of rapper Barrington DeVaughn Hendricks (a.k.a. JPEGMAFIA) is palpable in his erratic onstage antics, quippy lyrics and glitchy beats, solidifying him as one of the most intriguing contemporary hip-hop acts. His latest record, All My Heroes Are Cornballs, plays into the manic persona he's established with a tracklist packed with provocative song titles ("Jesus Forgive Me, I Am A Thot," "BasicBitchTearGas"), a kinetic collage of production styles and verses that touch on everything from police violence to The Dark Knight Rises. But the real attraction of JPEGMAFIA's work is his versatile voice and flow, which he puts to use in impressively unpredictable ways amid his glitchy, reference-ridden compositions. Rising Baltimore rapper and producer Butch Dawson opens the show.

Bob Dylan
Photograph: CC/Wikipedia/Piedmontstyle
Music, Folk, country and blues

Bob Dylan

icon-location-pin Credit Union 1 Arena at UIC, Little Italy, UIC
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Gruff folk poet Bob Dylan and his band return to Chicago, arriving on the heels of another salvo of Bootleg Series releases, Martin Scorsese's Dylan-centric Netflix film Rolling Thunder Revue and the 2017 covers album Triplicate, which pays tribute to the likes of Frank Sinatra, Nat King Cole and Billie Holiday. Though many of his recent concerts have favored newer material, Dylan has shown a fondness for latter day hits like "Highway 61 Revisited" and "Simple Twist of Fate" in recent years, performing sets packed with familiar tunes. His voice still isn't quite what it used to be, but it's still impressive to see a living legend exploring and reinterpreting his catalog with the help of a killer backing band. If you haven't had the pleasure of seeing Dylan before, don't think twice about snagging tickets.

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Theater in October 2019

Photograph: Michael Brosilow
Theater

A Doll’s House

icon-location-pin Writers Theatre, Suburbs
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If you saw A Doll’s House, Part 2 at Steppenwolf last year and left jonesing for the original work, the wait is over. This trim new adaptation of A Doll’s House from Sandra Delgado and Writers Theatre artistic director Michael Halberstam packs Henrik Ibsen’s early feminist classic into a brisk 90 minutes. Cher Álvarez stars as the stalwart Nora with Greg Matthew Anderson as her less-than-stalwart husband, Torvald.

Photograph: Christopher Semel
Theater

Sundown, Yellow Moon

icon-location-pin Raven Theatre, Edgewater
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With their father out of a job, twin sisters Joey (Diana Coates) and Ray (Liz Chidester) return home to try and keep their family in tune. Featuring music by the Bengsons, this Chicago premiere of Rachel Bond’s drama promises to keep those hot sticky summer vibes going well into fall.

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Steep Theatre Company
Photo: Grace Wiley
Theater

Mosquitoes

icon-location-pin Steep Theatre, Edgewater
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British playwright Lucy Kirkwood has a knack for pairing scientific inquiry with emotional upheaval. If you missed her astounding ecological drama The Children at Steppenwolf earlier this year, be sure to check out Mosquitoes, on tap at Steep Theatre. The play matches a conflict between two sisters up against the high-speed particles of the Large Hadron Collider—with collisions and explosions galore.

Photograph: Lowell Thomas
Theater

Brothers Size

icon-location-pin Steppenwolf Theatre Company, Lincoln Park
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Almost 10 years after the Brother/Sister Plays trilogy launched playwright (and occasional actor) Tarell Alvin McCraney to stardom, his riveting play Brothers Size makes its triumphant return to Steppenwolf. This Theater for Young Audiences production from up-and-coming director Monty Cole stars Patrick Agada, Manny Buckley and Rashaad Hall.

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Photograph: Keith Pattison
Theater

A Man of Good Hope

Cape Town’s Isango Ensemble takes up residence at Navy Pier with A Man of Good Hope at Chicago Shakes. Adapted from a novel by Jonny Steinberg, the chimera of musical and opera tells of a young Somali refugee, Asad Abdullahi, who escapes civil war only to find himself in the middle of more violence in South Africa.

Photograph: Joel Maisonet
Theater

Hell Followed With Her

icon-location-pin The Den Theatre, Wicker Park
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Horror movies are a reliable box-office draw, but the genre hasn’t always received as much love at the theater. But don’t tell that to the folks at Wildclaw, who have been churning out terrifying tales for over a decade. Their latest, written by local scribe Bill Daniel, mashes up Spaghetti Westerns and zombie flicks in the tale of a vengeful woman who finally tracks down her prey—only to find that the living dead are hot on her heels.

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Camera
Theater

Grey House

icon-location-pin A Red Orchid Theatre, Old Town
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Set in the remote mountains of Oregon, this world premiere from ensemble member Levi Holloway promises both fright and insight. After surviving a nasty car wreck, a couple takes refuge in a cabin that’s inhabited by four children and their caretaker. The safe space turns deadly as secrets from their past begin to unravel.

Photograph: Claire Demos
Theater

Kentucky

icon-location-pin The Gift Theatre, Jefferson Park
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Leah Nanako Winkler’s riotous Two Mile Hollow (which First Floor Theater mounted back in 2017) is one of the funniest shows this town has seen in years. In her play Kentucky, opening this month at the Gift Theatre, Winkler traces the exploits of another dysfunctional family. Almost-30-something New Yorker Hiro (Emjoy Gavino) decides to stop her 22-year-old Evangelical sister’s wedding back home in Kentucky. 

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Photograph: Courtesy First Floor Theater
Theater

Sugar In Our Wounds

icon-location-pin The Den Theatre, Wicker Park
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Donja R. Love’s Sugar in Our Wounds chronicles a queer romance between two black slaves in the Antebellum South. It’s part of a trilogy called The Love Plays* that chronicles same-sex relationships throughout African-American history. Directed by Mikael Burke, this Chicago premiere stars the always-electric Michael Turrentine as James, one of the lovers.

Photograph: Matthew Murphy
Theater

Latin History for Morons

icon-location-pin Cadillac Palace Theatre, Loop
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John Leguizamo has such boundless energy that he puts the Tasmanian devil to shame. In his Tony-nominated one-man show Latin History for Morons—touching down like a tornado for an abbreviated run in the Cadillac Palace Theatre—Leguizamo turns those energies loose on the blind spots of history books. Leguizamo tears through thousands of years of Latino history in search of a proper hero for his young son.

GYG Chicago TTD

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