Maceo Parker
Maceo Parker Photo: Nuccio DiNuzzo/Chicago Tribune
Aug. 29–Sept. 2
Jazz

Chicago Jazz Festival

The last two days of this annual showcase host some heavy hitters. Legendary pianist Ramsey Lewis performs his career finale on Saturday. The next day, trumpeter Jaimie Branch appears with her Fly or Die outfit, and P-Funk saxophonist Maceo Parker pops in to close out the fest.

Details:Loop. Grant Park. Free. chicagojazzfestival.us

Aug. 31–Sept. 1
Dance

Marlene Skog & Dancers

Skog’s contemporary ballet Consider It Not So Deeply evaluates the psyches of Shakespeare’s female characters using a mix of dance and spoken word, with original music by Matan Rubinstein and Chicagoland native Timothy Russell interspersed with Vivaldi.

Details:Near North. Ruth Page Center for the Arts. $10–$15. marleneskog.com

Sept. 1–16
Dance

Conference of the Birds

Having traversed 20 cities around the globe, choreographer Nejla Yatkin brings her Dancing Around the World series home to Chicago with a site-specific interactive performance on the lakefront. Audience members participate in guided movement inspired by flocking birds; the procession will become part of a short documentary by filmmaker Enki Andrews.

Details:South Loop. Caracol Gathering Space at Burnham Wildlife Corridor. Free. ny2dance.com

Sept. 5–8
Classical

Collaborative Works Festival

The vocal music organization Collaborative Arts Institute of Chicago spices up its annual celebration with the Midwest premiere of a song cycle by New York-based Missy Mazzoli, just named the Chicago Symphony Orchestra’s next composer in residence. The work in question is Songs from the Operas, a sort of greatest hits pulled from her operas Breaking the Waves and Proving Up. As for the usual maestros on offer, they include Mahler, Brahms, Schoenberg, Leoš Janáček, and Vaughan Williams.

Details:Various neighborhoods and venues. Free–$35 per concert; $60 festival pass. caichicago.org

Sept. 5–Oct. 28
Theater

Sweet Charity

Bob Fosse famously choreographed this 1966 musical and subsequent film about a “taxi dancer” looking for love in all the wrong places. Cy Coleman (music), Dorothy Fields (lyrics), and Neil Simon (book) combined forces for the show’s memorable highlights: the dead-eyed come-ons of “Big Spender,” the isolated undulations of “Rich Man’s Frug,” and the psychedelic grooves of “The Rhythm of Life.”

Details:Lincolnshire. Marriott Theatre. $50–$60. marriotttheatre.com

Sept. 6
Pop

Let’s Eat Grandma

It’s no surprise this British experimental pop group (consisting of childhood friends Rosa Walton and Jenny Hollingworth) is on a label called Transgressive Records. Its second studio album, I’m All Ears, is a collection of synth-heavy tracks that play as well at home as in a club. Incorporating elements of R&B and house, yet never falling squarely into either category, Let’s Eat Grandma proves there are still sonic curiosities in genres known for straightforward, mainstream appeal.

Details:Ukrainian Village. Empty Bottle. 8:30 p.m. $12–$15. eventbrite.com

Sept. 6
Rock

Mt. Joy

Thanks to its heavy and persistent touring schedule, this folky band has built a national fan base. On its self-titled debut album, which dropped this spring, Mt. Joy expands on the popularity of “Astrovan” (a single that’s racked up more than seven million streams on Spotify and counting) to prove its easygoing sound is destined for more than prime placement in a streaming service’s playlist.

Details:Pilsen. Thalia Hall. 7 p.m. $20. thaliahallchicago.com

Sept. 6–Dec. 15
Art

Martine Syms

This 30-year-old Los Angeles–based, Chicago-trained video artist is a rising star: Last year the New Yorker published an article about her online under the headline “How to Be a Successful Black Woman.” She returns to Chicago with Incense, Sweaters & Ice, a film, partially shot on location here, exploring Syms’s proposition that fashion, race, and the internet combine into a kind of everyday performance.

Details:Gold Coast. Graham Foundation. Free. grahamfoundation.org

Sept. 6–Dec. 16
Art

Yasuhiro Ishimoto: Someday, Chicago

Though Ishimoto, who died in 2012, is one of Japan’s most famous photographers, he’s not as well known to Chicagoans. This is odd, since he worked here for several decades. His socially aware, documentary-style photos of the city’s diverse communities are saturated with mood and grace.

Details:Lincoln Park. DePaul Art Museum. Free. museums.depaul.edu

Sept. 7
Rock

Car Seat Headrest

With 11 studio albums, two compilation albums, and two EPs, it’s difficult to believe Car Seat Headrest frontman Will Toledo is only 26 years old. But anyone who has heard his music — lo-fi, energetic indie rock with youthful spirit and sophisticated songwriting — knows Toledo’s age has little bearing on the quality of his output. His meticulous craftsmanship continues to disentangle surprises from songs that date back to the beginning of his career.

Details:Uptown. Riviera Theatre. 7:30 p.m. $25. ticketfly.com

Sept. 7
Opera

Stars of Lyric Opera at Millennium Park

For one night, cheapskates don’t have to look down from vertiginous heights to see Lyric singers. The company’s annual freebie offers excerpts from its season opener, La Bohème, this time around, with dreamboat Venezuelan conductor Domingo Hindoyan making his Lyric debut.

Details:Loop. Jay Pritzker Pavilion. 7:30 p.m. Free. lyricopera.org

Sept. 7–8
Festival

Windy City Wine Festival

Cap off your summer at this oenophilic gathering, where you can taste more than 300 types of vines from around the world. VIP ticket holders ($120) get to enjoy early admission and can pair their booze with special hors d’oeuvres.

Details:Loop. Buckingham Fountain. $15–$120. windycitywinefestival.com

Sept. 7–9
Dance

Breaking Grounds Performance Series

Emerging choreographers work together to make and then “wreck” each other’s dances to push the creative process into new territory. This series, inspired by house dance, martial arts, and contact improvisation, includes appearances by former Dance Colective company member Dina Liberatore and Dedrick Gray, who was recently featured in J’Sun Howard’s excellent Working on Better Versions of Prayers.

Details:Roscoe Village. Links Hall. $10–$40. linkshall.org

Sept. 7–16
Festival

Elgin Fringe Festival

More than 100 performances by more than 40 artists take over downtown Elgin for the northwest suburb’s fifth annual fringe fest, organized by Side Street Studio Arts. There’s also an extensive visual arts gallery and, on September 8, arts and crafts, games, and kid-friendly performances.

Details:Elgin. Various venues. $3–$10. elginfringefestival.com

Sept. 7–23
World

World Music Festival Chicago

Of all the free musical events the Department of Cultural Affairs and Special Events presents each year, this might be both the most rewarding and overlooked. It kicks off with a celebration of Indian classical music and dance that commences at 6 p.m. and ends at 8 a.m. the next day. On the last day, the fest hosts the scorching Congolese funk group Jupiter & Okwess and the Zhou Family Band, which plays traditional Chinese music with the energy of a New Orleans parade.

Details:Various locations. Free. worldmusicfestivalchicago.org

Sept. 8
Hip-Hop

Childish Gambino

To describe Donald Glover’s past three years as “successful” is an understatement. First, the comedy writer, standup, and actor debuted his surreal TV show Atlanta to critical acclaim (and a couple of Emmy wins). Then, under his Childish Gambino alias, he dropped “Awaken, My Love!,” a surprisingly successful collection of funk-infused R&B and hip-hop, including the instant classic “Redbone.” Those two projects were perfectly capped by Glover’s “This Is America,” a song that shot straight to the top of the Billboard charts in large part due to its video, which examines black American life and societal violence.

Details:Near West Side. United Center. 7:30 p.m. $120–$420. ticketmaster.com

Sept. 8
Rock

Rolling Blackouts Coastal Fever

Rather than focus on big choruses or vocal hooks, this Australian five-piece weaves catchy songs out of its serpentine guitar playing and propulsive drumming, crafting a mesmerizing sound as indebted to 1980s indie rock as contemporaries like the Brooklyn quartet Parquet Courts. The three “singers” speak or barely melodize cryptic lyrics about locations, relationships, memories, and desire — you know, typical rock ’n’ roll stuff.

Details:Lincoln Park. Lincoln Hall. 9 p.m. $15. lh-st.com

Sept. 8–Jan. 6
Art

Treasures from the White City: Chicago World’s Fair of 1893

This exhibit examines some of the more refined memorabilia from the legendary World’s Columbian Exposition — including silver pieces and leaded glass windows perfected by the prestigious Tiffany Glass Company — all displayed in an actual Gilded Age mansion.

Details:River North. Driehaus Museum. $10–$20. driehausmuseum.org

Sept. 10
Electronic

Gang Gang Dance

This New York–based trio has been around for nearly 17 years, and throughout that time, they’ve never been afraid to push the boundaries of their sound, veering from the eeriest corners of avant-garde, downtown-Manhattan music to the “easy listening” spectrum of house and pop. Lead singer Lizzi Bougatsos’s wails sound downright charming, and for all of Gang Gang Dance’s worldbeat tendencies, the tracks could easily fit on the dance floor of your favorite local club.

Details:Ukrainian Village. Empty Bottle. 8:30 p.m. $14–$16. eventbrite.com

Sept. 10–Oct. 13
Theater

Second Skin

In Western Springs native Kristin Idaszak’s world premiere for WildClaw Theatre, horror lurks in both the past and present. At the center of this macabre thriller are a dying mother and a daughter who finds herself awash in creepy childhood memories. Long-lurking secrets emerge from distant ancestors for a tale intent on scaring until Halloween arrives.

Details:Wicker Park. Den Theatre. $15–$30. wildclawtheatre.com

Sept. 11–Oct. 14
Theater

Tootsie

Here’s hoping this stage version retains the inspired nuttiness of the 1982 movie, wherein an out-of-work actor transforms himself into an actress to land a soap opera part and winds up becoming a feminist icon. Santino Fontana (a.k.a. Greg from Crazy Ex-Girlfriend) squeezes into a girdle for the lead in the Broadway-bound premiere.

Details:Loop. Cadillac Palace Theatre. $30–$155. tootsiemusical.com

Sept. 12
Classical

Considering Matthew Shepard

For his first major work, choral conductor Craig Hella Johnson has composed an evening-length oratorio about the gay college student whose 1998 murder in Wyoming spurred antihate legislation. Johnson twists the big-chord and rhythmic elements common to contemporary choral music into a modern Passion story.

Details:Highland Park. Ravinia. 7:30 p.m. $10–$60. ravinia.org

Sept. 12
Electronic

Jon Hopkins

Anyone who tells you that dance music can’t approximate the grandeur and scale of the symphony should pay attention to this British electronic artist, who’s contributed his distinct digital patches to bands as mainstream as Coldplay and figures as highbrow and esoteric as singer-songwriter King Creosote and art-pop producer Brian Eno. On his albums, Hopkins constructs elaborate, ominous, and interfused tracks that could light up a dance floor or your brain.

Details:Pilsen. Thalia Hall. 7:30 p.m. $22. eventbrite.com

Sept. 13
Classical

Lagrime di San Pietro

Peter Sellars, a stage director well known for his collaborations with composer John Adams, creates a staging of Orlando di Lasso’s 20-madrigal collection about Peter’s denial of Jesus. Sellars makes the story more about ordinary people than superhuman figures by supertitling the work with modern-language translations and directing the singers (from the excellent Los Angeles Master Chorale) to move around onstage.

Details:Highland Park. Ravinia. 8 p.m. $10–$45. ravinia.org

Sept. 13–14
Dance

Is/land

Three dancers of East Asian heritage join forces for That We Walk, which explores various narratives about home. Tourism videos sponsored by the U.S. government play in the background, a commentary on the complicated identities of the performers. Completing the program is Burrow, Tousle, two side-by-side solo improvisations from Lucky Plush’s Kara Brody and Amanda Maraist of Khecari.

Details:Roscoe Village. Links Hall. $15–$40. linkshall.org

Sept. 13–Oct. 21
Theater

Curve of Departure

At 94, Mike Nussbaum is Chicago’s most enduring leading man. Here, he stars as Rudy, the 80-something father of a man nobody much liked. In an airport hotel, Rudy meets with his late son’s wife and son as they grapple with their own mortality. Longtime Nussbaum collaborator BJ Jones directs the story of a family fraying at the seams.

Details:Skokie. Northlight Theatre. $35–$72. northlight.org

Sept. 13–Nov. 21
Art

David Hockney

The British master of pop art, perhaps best known for his cool depictions of nude men in Los Angeles swimming pools, brings his paintings to life with digital videos. A wall of high-definition TV screens blazes with vivid colors showing the seasonal changes of the woods near Hockney’s Yorkshire studio.

Details:West Town. Richard Gray Warehouse. Free. richardgraygallery.com

Sept. 13–Dec. 30
Art

The Time Is Now! Art Worlds of Chicago’s South Side, 1960–1980

This major exhibit reassesses the South Side as a hotbed for artistic innovation during the 1960s and ’70s. Here, the Black Arts movement emerged in the immediate aftermath of the civil rights era, Black Panther demonstrations, and the local radical jazz scene. Murals, prints, posters, photographs, and sculpture collectively tell a story of how concerted creativity animated a community during a period that changed Chicago art forever.

Details:Hyde Park. Smart Museum of Art. Free. smartmuseum.uchicago.edu

Sept. 14
Charity

Green Tie Ball

Chicago Gateway Green, a nonprofit that has worked for more than three decades to beautify highways and neighborhoods, puts on its signature annual fundraiser as the summer winds down. This year’s edition features flamboyant rocker Redfoo of LMFAO and a lengthy list of featured restaurants, including Chicago Chop House and Eli’s Cheesecake Company, in a verdant indoor-outdoor setting.

Details:Pilsen. The Geraghty. $175–$500. gatewaygreen.org

Sept. 14–16
Dance

Reboot

Margi Cole, Colleen Halloran, and Peter Carpenter — three Columbia College professors with serious choreographic chops — team up for an evening produced by Cole’s company, the Dance Colective. With his laughter-inducing, eyebrow-raising political bent, Carpenter constructs a new solo set for Cole that draws from current discourse surrounding truth, deception, and “alternative facts.” Halloran surveys similar territory in a rare new work.

Details:Albany Park. Dovetail Studios. $15–$20. margicole.com

Sept. 14–Oct. 27
Art

Edie Fake

Art collectors make a mad dash to any exhibit of new work by Fake, who rose to prominence memorializing Chicago’s gay and lesbian architecture in dazzling ink and gouache. For his second solo show at Western Exhibitions, he returns with jewel-like drawings that imagine the spaces where transgender people feel safe and thrive as a result.

Details:West Town. Western Exhibitions. Free. westernexhibitions.com

Sept. 15–16
Classical

The Mozart Requiem

A quartet of world-class opera star soloists bedizen Music of the Baroque’s season-opening concert: from soprano to bass, Amanda Majeski, Daniela Mack, Jonas Hacker, and Eric Owens. Opera junkies will know Owens as Wotan in Lyric’s Ring, Majeski from loads of local performances dating back to her time as a Northwestern undergrad, and Hacker from last season’s sold-out Fellow Travelers.

Details:Loop; Skokie. Sept. 15: Harris Theater; Sept. 16: North Shore Center for the Performing Arts. $10–$78. baroque.org

Sept. 15–16
New Music

Orson Rehearsed

The new-music group Fifth House Ensemble, which specializes in multimedia packaging for live chamber performances, premieres a work in progress by contemporary composer Daron Hagen about Orson Welles’s last hour of life. In this assemblage of fragmentary memories, three singers portray Welles, with instrumental and video accompaniment.

Details:Loop. Studebaker Theater. Free; reservations required. fifth-house.com

Sept. 15–Oct. 21
Theater

We’re Only Alive for a Short Amount of Time

In David Cale’s one-man autobiographical show, British singer Petula Clark (among others) and a backyard bird sanctuary provide a young boy respite from a troubled family and a bleak industrial town. Violence and beauty coexist in a monologue that fuses music with words and memories.

Details:Loop. Goodman Theatre. $20–$70. goodmantheatre.org

Sept. 15–Oct. 27
Art

Bethany Collins: Undersong

This rising multidisciplinary artist is known for altering printed text, whether by erasing specific words so that sentences take new meanings or creating small sculptures from scraps of sliced paper. For Undersong, her second solo exhibit at Patron, Collins explores rootlessness by modifying Homer’s Odyssey as well as old classified ads from former slaves looking for their lost family members.

Details:West Town. Patron Gallery. Free. patrongallery.com

Sept. 18–Dec. 9
Design

Up Is Down: Mid-century Experiments in Advertising and Film at the Goldsholl Studio

This show celebrates the golden age of advertising through the lens of a homegrown design giant. In the 1950s, Chicago was a hub for modernist graphic design, with Goldsholl and Associates being one of the best-known firms, churning out iconic logos for Motorola, 7-Up, and Vienna Beef. It even produced many of the era’s then-groovy, now-nostalgic educational short films.

Details:Evanston. Block Museum of Art. Free. blockmuseum.northwestern.edu

Riccardo Muti
Riccardo Muti Photo: Todd Rosenberg
Sept. 20
Classical

Concert for Chicago

The Chicago Symphony Orchestra kicks off its season with its annual free concert — back at Millennium Park, where past performances had been so packed that park staffers turned away even some early birds. Music director Riccardo Muti leads two famous overtures — Rossini’s William Tell and Tchaikovsky’s 1812 — sandwiching an operatic excerpt from Verdi, a guy Muti literally wrote the book on.

Details:Loop. Jay Pritzker Pavilion. 6:30 p.m. Free. cso.org

Sept. 20–Nov. 4
Theater

Downstate

Pulitzer Prize winner Bruce Norris’s world premiere explores the postprison lives of sex offenders trying to figure out a way to survive in a society that shuns them. The characters confront the limits of forgiveness and a road to redemption that might be a dead end.

Details:Lincoln Park. Steppenwolf Theatre. $44–$80. steppenwolf.org

Sept. 20–Nov. 4
Theater

Nell Gwynn

From heckler to star to king-adjacent power player, 17th-century actress Nell Gwynn was among the first women to (legally) take the stage in England. Her story — which includes a long-term liaison with King Charles — drew the ire of the Crown’s courtiers and the male actors she put out of work. She persisted nevertheless, succeeding on her own terms onstage and off. Christopher Luscombe directs the Olivier Award-winning script by British playwright Jessica Swale.

Details:Navy Pier. Chicago Shakespeare Theater. $60–$88. chicagoshakes.com

Sept. 21
Rock

Diet Cig

This pop-punk band from New York is as goofy and wild onstage as it is on record and on its Twitter page, which forgoes press information in favor of sporadic, off-the-cuff insight into the two silly minds that make songs with titles like “Pool Boyz” and “Tummy Ache.”

Details:Lincoln Park. Lincoln Hall. 9 p.m. $16–$18. lh-st.com

Sept. 21–23
Festival

Apple Fest

In addition to regular street-fair food, merchants at this fall fest sell all sorts of pomaceous treats, from apple cider doughnuts to apple lattes. The highlight of the annual event might be the apple-pie-eating contest, where contestants have to scarf down a whole pastry without using their hands.

Details:Long Grove. Old McHenry and Robert Parker Coffin. $5. longgrove.org/festivals/apple-fest

Sept. 21–29
Dance

Harvest Chicago Contemporary Dance Festival

Aerial Dance Chicago
Aerial Dance Chicago Photo: Antonio Perez/Chicago Tribune

Though groups such as Aerial Dance Chicago are on the bill, this showcase is noteworthy for the solo performers shining outside their companies: Corinne Imberski (ReDance), Jessica Miller Tomlinson (formerly of Thodos Dance), Michel Rodriguez Cintra (Lucky Plush), and others get to stretch their choreographic wings.

Details:Near North. Ruth Page Center for the Arts. $25. hccdf.com

Sept. 21–Oct. 6
Classical

Chicago Symphony Orchestra

The orchestra’s first three weekends of (indoor) concerts whirl out under the baton of Riccardo Muti, entering his ninth season as music director. Muti’s first program combines two Soviet composers, Prokofiev and Shostakovich. The second ties chestnuts by Mozart to one by Rimsky-Korsakov, his violin-tagged Scheherazade. The third conjoins Beethoven, Brahms, and the 20th-century modernist Paul Hindemith. The Symphony Ball concert and gala rounds up the city’s ballers on October 6.

Details:Loop. Symphony Center. $15–$120. cso.org

Sept. 21–Nov. 4
Theater

Indecent

In 1923, the Broadway debut of God of Vengeance set off a firestorm of condemnation — its lesbian love story was regarded as filth by both critics and audiences. Pulitzer winner Paula Vogel (How I Learned to Drive) has seven actors and three musicians playing more than 40 roles as they re-create the events surrounding the play and dramatize the heroism of artists who risked their careers and even their lives to bring God of Vengeance to the stage.

Details:Lincoln Park. Victory Gardens Theater. $20–$65. victorygardens.org

Sept. 22
Hip-Hop

J. Cole

In recent years (and especially on KOD, his fifth studio album), this emcee has doubled down on his signature earnestness, grappling with the culture of drug abuse, addiction, and depression that has gripped the minds of popular Gen-Z SoundCloud rappers and their fans. As always, Cole runs the risk of being too preachy in his verses, but he is able to rein it in, for the most part, with bursts of self-reflection.

Details:Rosemont. Allstate Arena. 7:30 p.m. $49–$275. ticketmaster.com

Sept. 22–Oct. 28
Theater

Caroline, or Change

Set in 1963, this Tony-nominated musical by Tony Kushner and composer Jeanine Tesori infuses politics (JFK’s assassination looms large) with whimsy (a singing washing machine) for an emotionally rich story of a black maid and an 8-year-old Jewish boy devastated by the death of his mother. Tesori uses everything from Motown to Jewish folk tunes to tell a tale of love and loss, performed here by Firebrand Theatre.

Details:Wicker Park. Den Theatre. $20–$45. firebrandtheatre.org

'Hairy Who? 1966–1969'
Hairy Who? 1966–1969 Photo: The Art Institute of Chicago, The Lacy Armour and Samuel and Blanche Koffler Acquisition funds, the Estate of Walter Aitken, © Jim Nutt
Sept. 26–Jan. 6
Art

Hairy Who? 1966–1969

There was something delightfully weird about the Hairy Who, the first distinctive art movement to emerge from Chicago in the 1960s. The era was marked by urban grit, social tension, and sexual liberties, so Jim Nutt, Karl Wirsum, Gladys Nilsson, Jim Falconer, Art Green, and their peers responded with an unrestrained take on the city’s blues scene, smutty streetwalkers, and surreal flea market finds. This is the first major survey of their work, with more than 200 pieces representing an astonishing vision.

Details:Loop. Art Institute of Chicago. $14–$25. artic.edu

Sept. 27–30
Art

Expo Chicago

If you can’t visit art galleries in Hong Kong, Berlin, London, and Stockholm this year, then consider Chicago’s international contemporary art fair your one-stop shop for some of the edgiest art being made today. More than 100 galleries attend, rounded out by special programming with artist and curator talks — don’t miss Theaster Gates reflecting on Chicago’s midcentury design history on September 28.

Details:Near North Side. Navy Pier. $20. expochicago.com

Sept. 27–30
Dance

Hubbard Street Dance Chicago

The company featured in this month’s fashion preview gets a little funky for its fall series, with a new piece by Canadian choreographer Emma Portner, street-dance star Lil Buck, and So You Think You Can Dance choreographer Jon Boogz. The work is inspired by environmental sustainability and Paul Stamets’s Mycelium Running, a manual and manifesto about mushrooms, and scored with original music composed by Devonté Hynes (a.k.a. Blood Orange) and performed by Third Coast Percussion.

Details:Loop. Harris Theater. $25–$110. hubbardstreetdance.com

Sept. 29–Oct. 2
Opera

Serse

Haymarket Opera Company has introduced Chicago, not to mention the modern era, to several resurrected baroque operas, but here the company engages a work so mainstream that even Lyric once performed it — albeit 23 years ago. Handel’s opera Serse concerns not Circe or any Lannisters but King Xerxes of Persia, opening with his ode to a plane tree, “Ombra Mai Fu,” known to the loosely acquainted and specifically to readers of Our Town as “Handel’s ‘Largo.’ ” Mezzo-soprano Suzanne Lommler plays the title character.

Details:Loop. Studebaker Theater. $10–$85. haymarketopera.org

Through Sept. 30
Theater

Radio Golf

Sorrow, anger, and gentrification are inextricably linked in the final installment of August Wilson’s 10-play Pittsburgh cycle. Battles over real estate, eminent domain, and municipal politics might not sound like the subjects of riveting drama and poetic language, but Wilson skillfully achieves both.

Details:Hyde Park. Court Theatre. $20–$74. courttheatre.org