Resuming our roundups of art from American cities, we realized that we wanted to highlight the remarkable people who have made our artistic traditions great, as well as the wonderful places where art can be enjoyed.

That’s why we’re back with a roundup of Chicago artists, organized from the nineteenth-century architect who forever changed the face of Chicago to the electric guitar-shredding star who is revolutionizing the blues music scene.

Read on to learn about nine amazing Chicago artists! Along the way, you’ll discover many of the city’s cultural institutions, so you can still rely on us for your next Chicago itinerary, too.

Daniel H. Burnham, Architect (1846-1912)

Soon after Chicago reached one million residents, Daniel H. Burnham supervised the 1893 Chicago World’s Fair, which established its reputation as a great American city. “Make no little plans” was Burnham’s motto, but his career began with rejected college applications, fruitless mining work, and a failed campaign for the Nevada Senate. Burnham’s luck changed at his architectural firm. With colleagues, he designed one of the first skyscrapers, the 10-story Montauk Building (1882-83), and drafted the 1909 Plan of Chicago. Ultimately, Burnham’s projects set the agenda for urban development both in Chicago and around the world.

Georgia O’Keefe, Painter (1887-1986)

After one year at the School of the Art Institute of Chicago, Georgia O’Keefe lived and worked in a variety of American cities. Although O’Keefe painted landscapes and evocative symbols of the Southwest, she is best known for her instantly recognizable flowers, such as Jimson Weed/White Flower No. 1. Typically, critics have seen the flowers as images of female sexuality, but one dissenter from across the pond takes pains to point out that, usually, “the centres of the flowers … are androgynous and thus not exclusively feminine.” We don’t doubt the botanical fact – just its decisiveness for art interpretation. At any rate, a range of O’Keefe’s works beyond the iconic flowers can be viewed at the Art Institute of Chicago, which rightly ranks its former student among the greatest 20th-century American painters.

Sandra Cisneros, Writer (b. 1954)

A Chicago native and alumna of Loyola University, Sandra Cisneros has won numerous awards, including the prestigious MacArthur Foundation Fellowship. Her novel The House on Mango Street, already known to generations of students, will soon have an operatic adaptation. According to a biographical statement from Poetry Foundation, which awarded Cisneros one of its $100,000 Lilly prizes in 2022, the author “chose to have books instead of children.” American literature has been enriched by her decision – and so, presumably, have been the four small and clearly beloved dogs who are Cisneros’ domestic companions: Luz de Mi Vida (Light of My Life), Osvaldo Amor, Nahui Ollin, and Leopoldine Puffina. Now, we all know where to find A House of My Own, Cisneros’ latest book. But where can we see some pet photos?

The Second City, Improv Company (est. 1959)

In the wake of A.J. Liebling’s harsh Chicago: The Second City (1952), a small band of merrymakers reclaimed the moniker for their improv theater, which has seeded the cast of Saturday Night Live since its first broadcast in 1975. Second City alumni include Tina Fey, Jane Lynch, Catherine O’Hara, Suzy Nakamura (born in Chicago), Amy Poehler, Sam Richardson, and Stephen Colbert, who started answering phones for Second City in 1987 and now chairs its Artistic Advisory Board. Thus, while people are still reading Liebling’s diagnosis of Chicago’s “first-or-nothing psychology,” you might say Second City remade Chicago as the City of the Last Laugh.

Steppenwolf Theatre Company (est. 1974)

If you recognize the names of some of the Steppenwolf Theatre Company’s earliest members – Gary Sinise, John Malkovich, Laurie Metcalf – then you can easily imagine why the ensemble soon needed a larger and more permanent performance space. After mounting productions in several churches, the Steppenwolf Theatre Company secured a 134-seat auditorium at the Jane Addams Center in 1980 before moving to its own theater in Old Town in 1991. Over the years, the ensemble has earned numerous Tony Awards®, including Best Director (Play) and Best Play for Grapes of Wrath (1990), Best Revival for One Flew Over the Cuckoo’s Nest (2001), and five separate awards for August: Osage County (2008). (Its playwright, Tracy Letts, also won a Pulitzer.) In November 2021, Steppenwolf expanded yet again, opening the Liz and Eric Lefkofsky Arts and Education Center. We can’t wait to see what will come next from Chicago’s most celebrated theatre company!

Jennifer Hudson, Actor and Singer (b. 1981)

For a world-class example of performing arts excellence, we’d be hard-pressed to find a stronger candidate than Jennifer Hudson. After appearing on American Idol (2004 season), Hudson was selected to portray Effie Melody White in the 2006 film adaptation of the Broadway musical Dreamgirls. The performance earned Hudson an Oscar®, a Golden Globe®, and other prestigious awards. Two years later, her album Jennifer Hudson won the 2009 Grammy® for Best R&B Album. Her star has appeared on the Hollywood Walk of Fame since 2013, and Hudson followed this honor by appearing among the cast for The Color Purple, which won the 2017 Grammy® for Best Musical Theater Album. We’re breathless simply trying to recite the accomplishments of this Chicago-born superstar!

Flor, Visual Artist (b. 1989)

The mixed-media artist Flor, whose earlier works appear under the name Alejandro Jiménez-Flores, was born in Mexico but educated in Chicago, where they have continued their career. After graduating from the University of Illinois, Chicago, with a Bachelor of Fine Arts (BFA) in 2012, Flor completed a 2015 residency with Artists’ Cooperative Residency & Exhibitions (ACRE) and has exhibited or performed work at venues including Gallery 400 and Chicago’s Museum of Contemporary Art. Perusing Flor’s work, we’re thrilled by its vibrant colors and intricate patterns. We’ll avidly follow the adventures of Kiki, the monarch butterfly featured in Flor’s recent works.

Cole Bennett, Music Video Director (b. 1996)

Cole Bennett’s company Lyrical Lemonade is a wildly successful producer of music videos and, yes, a vendor of the tart yet tasty beverage. Bennett started Lyrical Lemonade as a YouTube channel while attending high school in Plano, IL, just west of Chicago. Lyrical Lemonade began humbly by documenting Chicago’s hip-hop scene, but today, Bennett’s proudly independent studio not only ushers in new talents, such as Juice WRLD and Lil Pump, but also works with long-established stars, such as Eminem. Despite pressures to relocate from Chicago to L.A. or NYC, Bennett firmly believes in “trying to give back to the city” that fostered his love for music. Lyrical Lemonade will likely remain just as integral to Chicago culture as it is to the global hip-hop industry.

Melody Angel (b. 1990 or 1991), Blues Musician

While continuing the blues tradition, created as Black Americans moved to Chicago during the 20th century, Melody Angel (her birth name) also breaks the mold for musical stars. As she explained, “a Black woman playing electric guitar” is, according to conventional wisdom in the recording industry, “not sellable.” Undaunted, Melody Angel sings while playing lead guitar, and it’s easy to see – or, rather, hear – why she represents “the future of the blues.” Channeling Jimi Hendrix and Big Mama Thornton, Melody Angel gives the world blues music for a new millennium.

That’s our Chicago artists roundup! As you can see, the city has come a long way from poet Carl Sandburg’s  ambiguous praise of it as “City of the Big Shoulders.”

Of course, CreativeFuture still cherishes – and closely identifies with – Chicagoans’ alleged propensity for “[f]linging magnetic curses amid the toil of piling job on job.” We’re happy, though, to take periodic breaks so that we can remember our country’s amazing artists.

Until next time, find some creativity wherever you can. Stay safe, and be well. #StandCreative