As fall approaches Chicago and the temperatures tick upward one last time before the inevitable cold slump, the city enters into a rallying cry. Chicago Exhibition Weekend returns today, with 50 participants hosting concurrent programming across the city through this Sunday, September 21. But even with excitement stirred, it can feel confusing to celebrate the arts at this time. President Trump’s threat of National Guard deployment and surges of ICE raids cast a shadow on the festivities as protesters fill the streets. The art world doesn’t hold all the answers, but creativity is always worth the endeavor. As much is clear in the artists and shows featured in this guide: Theaster Gates, whose practice of nurturing stories is more relevant than ever; Destyni “Desi” Swoope, who reminds us that community is immutable; the outsider art at Sawhorse and Shanghai Seminary, proving that artmaking persists as a practice of self-preservation. Whether in probing structure, like Tongji Philip Qian, or imagining different states of being, like the Symbolists, art always has the power to pay attention in the face of adversity. So get out there if you can, Chicago.Secondary PurposeSawhorse, 4222 West Fullerton Avenue, Chicago, IllinoisThrough October 26Installation view of Secondary Purpose (photo Natalie Jenkins/Hyperallergic)Featuring over 80 works selected from the personal collection of Chicago innkeeper and photographer Ray Reiss, this dense exhibition packs a lot of heart. The collection trends toward folk and self-taught art. Reiss acquired many of the objects from thrift stores and antique shops — atypical sources for work that inhabits gallery spaces. While some pieces are by better-known outsider artists, such as Mr. Imagination and Lee Godie, several are from unidentified creators. The amusing animals, earnest depictions of people, and esoteric landscapes of Secondary Purpose create an atmosphere of comfort and joy. According to Reiss, the best thing to do with the work is to “just sit there and feel it.” The Gloaming Western Exhibitions, 1709 West Chicago Avenue, Chicago, IllinoisThrough November 1Journie Cirdain, “Chandelier (Dewdrops)” (2025) (photo Natalie Jenkins/Hyperallergic)The beautifully rendered graphite drawings of Journie Cirdain’s The Gloaming seem steeped in magic. Some offer a bit more narrative, such as “Amends,” featuring a crouched naked woman with her head fit snugly inside the open jaws of a wolf. Others dedicate their focus to extremely particular subject matter, and in doing so, are startlingly evocative. “Chandelier (Dewdrops)” transforms a spiderweb into a glittering cosmos of dew against a darkened background. The narrow attention on the small yet magnificent natural phenomenon of condensation on spider silk is divine, traversing the thin line between the mundane and otherworldly.UrbaniteWeatherproof, 3336 West Lawrence Avenue, #303, Chicago, IllinoisThrough November 2Krista Beinstein, “Momente 1” (image courtesy Krista Beinstein)In a strange but potent clashing of the vulnerable, violent, and erotic, Weatherproof curators Milo Christie and Sam Dybeck have paired photographer Krista Beinstein with sculptor Tarik Kentouche. Beinstein’s work explores queer eroticism; her pornographic film photographs are unabashed in their bold depictions of subjects in fetish wear striking brazenly sexual poses. Juxtaposed with Kentouche’s “Civilians” — stuffed monkeys that one might win at a county fair, armored with soldered glass outfits — the photographs open to new dimensions of innocence and sincerity. The blank, guileless expressions of the monkeys, frozen in their rigid outfits, make them perpetual observers, which seems eerily similar to our state as consumers. It’s an unexpected pairing for a duo show, and yet, thrillingly, it works. Sympathy RibbonGrunts Rare Books, 1500 South Western Avenue, Suite 403, Chicago, IllinoisThrough November 9Installation view of Sympathy Ribbon (photo Natalie Jenkins/Hyperallergic)Light and memory are roused in Sympathy Ribbon, a show that pairs artists Madeline Gallucci and Margaret Crowley. The exhibition title comes from a haunting work by Crowley: a found sympathy ribbon. Typically attached to caskets or funerary floral arrangements, these ribbons are intended to adorn memorial goods and signify the relationship between the sender and the deceased. Crowley’s ribbon reads “Husband” in gleaming gold lettering. It’s unsettling to consider how an object so mass produced could carry the weight of something as meaningful as a lifelong relationship, but as the ribbon flaps gently in the gallery its airiness complements the play of light, color, and depth in Gallucci’s inscrutable layered paintings. The harmony begs for a moment of pause. Recent WorksShanghai Seminary, 3262 South Morgan Street, Chicago, IllinoisThrough November 22Winifred Mason, “Untitled” (2022), ink and collage on paper (photo Natalie Jenkins/Hyperallergic)Humorous, clever, and refreshingly honest, this survey of recent works by Chicago-based artist Winifred Mason is equal parts social commentary and inside jokes. For the past 30 years, Mason has been utilizing the same text, collage, and drawing process to create a series of pared-down images that process the constant influx of information she receives, whether through the newspaper, a news broadcast, or simply through her window. This process has allowed Mason to cover a wide range of topics reflecting the unpredictability of the endless media one consumes, and the impact of that consumption on our own thought patterns. Sometimes, that translates as a wish: “We want our kids to be safe & unspoiled,” one work declares; two others read, “we’re convinced of a new miracle remedy for a sore throat (drink pickle juice)” and “a broken heart (close your eyes and draw a picture of Christ).” Krapfen The Renaissance Society, 5811 South Ellis Avenue, Chicago, IllinoisThrough November 23Installation view of Diego Marcon: Krapfen (photo Natalie Jenkins/Hyperallergic)Come with an appetite to Italian artist Diego Marcon’s United States debut. On the menu? Krapfen, a German jam doughnut. Marcon’s video installation plies its main character with increasingly urgent demands to eat the sugary treat, communicated through an original Italian-language opera-inspired composition. As the song progresses, clothing items come alive around a highly staged childhood bedroom, where it’s difficult to distinguish what’s real from what’s animation. At once whimsical and unsettling, Krapfen consumes its visitors through a marigold paint job fully covering the Renaissance Society’s cathedral-like interior, leading to a dizzying down-the-rabbit-hole sensibility amid the unusual soundtrack, strange characters, and vast yellow expanse. Alloyed CommitmentsLogan Center Exhibitions, 915 East 60th Street, Chicago, IllinoisThrough December 7Installation view of Alloyed Commitments (photo Natalie Jenkins/Hyperallergic)Upon entering Tongji Philip Qian’s Alloyed Commitments, viewers encounter a large wall drawing that counts the passing of minutes. This establishes the show’s central concern: time. The clock reads “…It is twenty-eight to two. It was twenty-eight to two. It is twenty-seven to two. It was twenty-seven to two…” and so forth. As Qian reveals in a notarized affidavit elsewhere in the show, the title of the wall work, “No-risk Hour,” refers to the period during Daylight Savings Time when an extra hour is gained. This no-risk hour is particularly important for Qian; he utilizes the phenomenon to race the clock as an artist, producing works under particular parameters during this period. There’s a certain beauty in his attention to process, structure, and legibility through time — he’s capturing existence within its relentless passage. Strange Realities: The Symbolist ImaginationThe Art Institute of Chicago, 111 South Michigan Avenue, Chicago, IllinoisThrough January 5, 2026Gustav Adolf Mossa, “Self-Portrait or Psychological Portrait of the Artist” (1905); Regenstein Endowment Fund, Buchanan Family Foundation in honor of Viviane Van Leer Kellermann (image courtesy Art Institute of Chicago)Strange Realities: The Symbolist Imagination draws upon the Art Institute’s diverse collection of drawings and prints to bring much-needed attention to Symbolism, a 19th-century art movement that rejected rationalism and emphasized emotional experience. The sweeping show of works on paper features fantastical imagery, frightening creatures, and mythological references. A sinister example is Jean Delville’s “Medusa,” in which the ghostly mythological figure offers the twisting, thirsty snakes on her head two small dishes of liquid as tendrils of smoke curl out from pomegranates around her. The avant-garde approach to imagery is reflective of Symbolists’ pessimism toward modern society and their desire to escape reality — inclinations that should resonate with many viewers today. Theaster Gates: Unto TheeSmart Museum of Art, 5550 South Greenwood Avenue, Chicago, IllinoisThrough February 22, 2026Glass lantern slide from the University of Chicago’s Department of Art History, now in the care of Theaster Gates (courtesy the Rebuild Foundation)On the heels of the successful inauguration of The Land School, a South Side hub for creative experimentation championed by Theaster Gates, comes yet another monumental project for the artist — his first solo museum exhibition in Chicago. It’s particularly meaningful to see the artist’s multidisciplinary work in his hometown. A core part of his practice is archival, as he seeks to activate the lives of objects with cultural significance or charged histories, often from Chicago. Some of the materials reactivated in the show include old glass lantern slides from the University of Chicago Department of Art History and archival materials from the Johnson Publishing Company, a Black-owned company that published the iconic Ebony and Jet magazines and was headquartered in the city. As a professor of Visual Arts at the University of Chicago, Gates is uniquely positioned to question collection and creative practice in relation to the school, proving how artists can find and preserve meaning in objects that are adjacent to the institution. Abuela’s HouseNational Museum of Puerto Rican Arts and Culture, 3015 West Division Street, Chicago, IllinoisThrough July 18, 2026Destyni “Desi” Swoope, “Sunday Sewing” (courtesy Destyni Swoope)In her museum debut, Destyni “Desi” Swoope celebrates Caribbean heritage, collective memory, and enduring intergenerational bonds. Vivid scenes of community make up Abuela’s House. In “Heirloom,” brightly manicured hands reach across a colorful patchwork table to pass dominoes stamped with the Puerto Rican flag. Another work, “Sunday Sewing,” features the turned back of a woman wearing a floral shirt; she sits at a table with coffee and strawberries as she feeds string through a light pink sewing machine. The immediate and intimate nature of the compositions makes them feel like direct takes from Swoope’s memories. They’re further animated by the artist’s distinctive mixed-media approach, which imbues the imagery with playful textures, dimensions, and materialities, emphasizing the liveliness and joy of kinship.