The Ultimate Art Insiders’ Guide to Chicago

Chicago shimmers and glows with its multifaceted cultural opportunities for the arts-minded traveler, especially in late summer, when fair skies and Chicago Exhibition Week make traversing the city’s vibrant neighborhoods particularly enjoyable. Known as CXW, the seven-day event, from September 14 to 20, is the brainchild of philanthropist and entrepreneur Abby Pucker, a member of Chicago’s Pritzker dynasty. (Her mother is film producer Gigi Pritzker, and one of her cousins is Illinois Governor J. B. Pritzker.)

Pucker, a board member of MoMA PS1 and a patron of many other New York and Chicago institutions, created the arts organization Gertie with several goals in mind. In addition to running CXW, it arranges shows open to all and has a membership program that provides special access to events, exhibitions, and educational courses geared toward collectors. “You need a guide to lift the veil a little bit,” says Pucker of why she started Gertie. “Chicago will give you the world if you scratch the surface.”

The Windy City is rightfully revered for its top-tier museums, such as the Art Institute of Chicago, which houses one of the world’s most staggering permanent collections; beginning in September, it will spotlight work by Mary Cassatt. More cutting-edge tastes are served by the Museum of Contemporary Art Chicago (MCA). “Chicago is more humane but no less brilliant than other major cities,” says Madeleine Grynsztejn, director of the institution, which is hosting the exhibition “Slow Dance” with artists who use performance “to reclaim forms of slowness that resist the contemporary demand to constantly perform.” On view September 12 to March 21, 2027, the showcase features the work of Brendan Fernandes, Gordon Hall, and Geumhyung Jeong, among others.

Grynsztejn’s theory is that Chicago’s location in the middle of the country has forced people to do their own thing with confidence. “Geography is destiny,” she says. “There’s a self-sufficiency to the ecosystem.”

John Corbett, cofounder of local gallery Corbett vs. Dempsey, notes one of the reasons for the high quality of local exhibitions is the freedom their location brings in terms of working with other art spaces. “For us as dealers, we have this major institutional infrastructure, but we’re not on anyone else’s turf,” he says. “An artist from a mega-gallery can do an unusual show here that they wouldn’t in their natural habitat.”

One such institution is the jewel-box museum Wrightwood 659, a former apartment building on the North Side that was spectacularly converted by Pritzker Prize–winning architect Tadao Ando in 2018. Its programming frequently focuses on LBGTQ+ artists and issues, such as its recent show of the late, great painter Martin Wong. This fall, “Inner Worlds: Visions from the Hirshhorn Museum Collection” highlights works by three groundbreaking women artists—Yayoi Kusama, Niki de Saint Phalle, and Mary Bauermeister; it runs September 25 to December 19.

The South Side neighborhoods offer a cultural treasure trove that too few visitors experience, starting with the Smart Museum of Art at the University of Chicago, a small but expertly curated collection on a gorgeous campus; a survey of work by the art collective teamLab opens on September 22. The Renaissance Society, an independent museum founded in 1915 and housed in a lovely Gothic stone building on campus, is “one of the country’s biggest hidden gems,” says Chicago gallerist Monique Meloche. Artist Maurizio Cattelan organized the society’s spring benefit, which included an hour and a half of mandatory silence, an example of the quirky texture that smaller institutions bring to the overall scene.

Then there are the unique contributions from world-renowned Chicago artist Theaster Gates, who is heralded for his devotion to social practice. His Rebuild Foundation has created two venues unlike any other: the Stony Island Arts Bank and the Land School. Both are community arts incubators that also host offbeat exhibitions and other programming. For instance, one current experiment at the Land School is “A Listening Space,” an immersive project encompassing hundreds of vinyl records as well as hot tea and cozy furniture, which encourage visitors to show up and hang out. It is further evidence of the artist’s stated principle of “radical hospitality,” a concept that is Chicago to its very core.

With the June opening of the Obama Presidential Center, the South Side has added another globally important art destination, as the building, designed by Tod Williams and Billie Tsien, is filled with site-specific works by leading painters, sculptors, and installation makers, with a strong representation of Chicago talents. Inside the nearly billion-dollar project, Gates’s 175-foot mural frieze is displayed alongside commissions by Julie Mehretu, Mark Bradford, Idris Khan, and many others.

The tight-knit artist network is part of what fuels the city’s unusually warm and productive atmosphere, and no one is ever more zealous than a convert. “People want to support you here, and there are a lot of points of entry,” says Brendan Fernandes, who was born in Nairobi, Kenya; raised in Toronto; and lived briefly in New York before moving to Chicago ten years ago. Esteemed for incorporating dance into his cutting-edge practice, Fernandes mounts a September slate in Chicago that includes the show at the MCA, a solo presentation at Monique Meloche, and an ongoing project at the Driehaus Museum, an institution celebrating art and collectible design in two landmark buildings just steps from the city’s Magnificent Mile.

Fernandes has been known to go bowling the day after Thanksgiving with Pucker and the artist couple Nick Cave and Bob Faust, a typical bit of camaraderie among the city’s creative class. Cave—one of the most prolific museum exhibitors of the past decade, famous for his over-the-top installations made of hundreds or thousands of carefully chosen objects—has lived in Chicago for nearly 40 years.

He makes the point that having established artists like himself, Gates, and Fernandes is great, but he is most reassured by the way that people like Pucker are seeding the ground for the future. As he puts it, “I am seeing the next generation step up. They are finding their way and looking at the bigger picture.”

A version of this article first appeared in print in our 2026 Fall Issue under the headline “Towering Above.” Subscribe to the magazine.