No matter where you live or stay in this city, you probably won’t go more than a couple of blocks without seeing Chicago street art. Whether it comes from a new, young artist tagging an alleyway or an established muralist whose colors climb up the side of a ten-story building, talented painters splash this city with art and color at every turn. And, because each neighborhood carries its own heritage and history, that background enters into the art and brings it to life.
Here are a few of the top spots to check out Chicago’s rich street art culture.
Looking to move to Chicago so that you can explore the Chicago street art scene? Reach out to AptAmigo, and we will help you find your dream apartment stress-free.
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Neighborhoods with Can’t-Miss Chicago Street Art
Rogers Park
If you ever find yourself in the north side of the city on a quiet afternoon, we highly recommend that you take a stroll down the Mile of Murals. A community-based art initiative located in the Rogers Park neighborhood, this outdoor exhibit breaks each section of street art into separate themes, such as “Be Happy” or “Resilience.”
Amongst these installations, one favorite jumps out right away. The 2016 project for the Mile of Murals emerged out of a collaboration with New York’s Audubon Mural Project. Located at Greenleaf and Glenwood, the artists created a bird inspired mural that showcases all of the birds in Chicagoland endangered by climate change. Murals that inspire and inform always top our list of must-sees.
A locally famous Chicago street artist named Hebru Brantley also created a mural called “Respiration” in Rogers Park. Commissioned by the Rogers Park Business Alliance (a huge sponsor of the Mile of Murals), this installation is tucked under the Redline tracks at Ravenswood and Pratt. Locals know Brantley best for his easily identifiable character of a young, goggle-wearing boy named Flyboy, ready to take off at a moment’s notice. In a creative blend of modern pop art and Japanese anime, Flyboy always looks ready to take on the world. “Respiration” depicts multiple Flyboy-style characters riding alongside and on top of the well-known Chicago Transit Authority trains, a captivating and quirky find.
Take Me There:
South Loop
When the average person thinks of Chicago, they picture the bustling downtown shopping centers along Michigan Avenue and the famous sculpture “Cloud Gate,” known more popularly as “The Bean.” So, if you find yourself feeling torn between seeing the buzz of the downtown area or perusing an art gallery, don’t fret. You can experience both thanks to the Wabash Arts Corridor in the South Loop neighborhood. Otherwise known as WAC, this collection of 20+ murals covers buildings with Chicago street art over the span of 7 blocks on Wabash Street. With most of these murals representing collaborations between multiple artists, local galleries, and the nearby Columbia Arts College, the amount of talent that went into these installations is breathtaking.
In one of the WAC murals, the winner of a 2014 art competition, former Columbia student Jacob Watts, got the chance to create the almighty “Moose Bubblegum Bubble.” Just like its namesake suggests, it is a gigantic mural of a moose, blowing a bright pink bubble gum bubble. We can’t think of anything more lighthearted than this pop (!) culture meets photo-realism piece of art. Located at 33 E. Ida B. Wells Drive, viewers will walk away with plenty to chew on over this one.
Similar to the Audubon mural in Rogers Park, another piece created for WAC also embraces nature and speaks to our Midwestern soul. Hailing from the Netherlands, artist Collin van der Sluijs flew west for the winter to create this beautiful homage to the Illinois rolling meadows. “From Doom to Bloom” depicts two birds perched on gorgeous native flowering vines that scale the side of a building at 1006 S. Michigan Ave. Both birds painted are considered endangered species, so this mural is not only beautiful, but also reminds us of the importance of conservation.
Take Me There:
Wicker Park
If you ever wondered where Chicago’s hipsters reside, look to Wicker Park. In fact, Forbes placed it in fourth on their list of “America’s Best Hipster Neighborhood” in 2012. The street art located in this hippest of neighborhoods can feel a little tricky to find. Wicker Park makes you work for it, but it is definitely worth the effort.
JC Rivera, AKA “The Bear Champ” is Wicker Park’s most recognizable artist. His rough and tumble city street bears give off a tough and tender vibe, much like many lifelong Midwesterners. The best part: if the bear’s paws make it into the mural, they almost always sport boxing gloves. While his bears have foraged their way into many different neighborhoods in the city, Rivera’s association with Wicker Park stands out. One example of his trademark art can be found at 1414 N. Milwaukee Avenue, where a colorful swirl of wispy purple and pink clouds hold three grumpy bear heads, all with little Band-Aids on their foreheads. Try and count all of Rivera’s bears on your trek through the city.
Take Me There:
Bucktown
Just a stone’s throw away from Wicker Park sits its next-door neighbor, Bucktown. This neighborhood maintains that same hipster vibe, while also housing the treasure that is the “Greetings from Chicago” mural. Created by muralist Victor Ving and photographer Lisa Beggs, it is an iconic must-see for anyone visiting the Windy City. Reminiscent of an old-school postcard, this mural encases a different element of classic Chicago nostalgia within each letter. From the city skyline to the Cubs and White Sox logos, it appeals to tourists and Chicagoans alike. You can’t miss this recognizable street art located on Milwaukee Avenue.
Looking for more photo spots like this one? Check out our pick of the most Instagrammable spots in Chicago.
Take Me There:
Pilsen
A neighborhood drenched in history, Pilsen shows off its heritage through long stretches of Chicago street art along its 16th Street rail embankment, among many other locations. This neighborhood’s murals reflect its character as a melting pot of culture.
Operating out of a studio in Pilsen, street artist Joseph Perez, A.K.A. “Sentrock,” has plastered his easily recognizable bird masked character, known as the Bird City Saint, all over Chicago. This character represents freedom and empowerment, and Sentrock often places it with political intention. Most of Sentrock’s art aims to empower the community and bring light to important issues.
Made by locally renowned artist Jeff Zimmerman, another installation worth seeing is “Increíbles las cosas a se ven,” or “Oh, the Things You’ll See.” This mural stretches the length of a building on 19th and Ashland. It details the religious, social, and political character of the families that live in the neighborhood. With the inspirational phrase, “Si, se puede,” which translates to, “Yes, you can,” this painting reminds anyone who sees it that anything is possible.
Take Me There:
Immerse Yourself in Chicago’s Art-Filled Streets Every Day
If you’re looking to move to this street art savvy city, let AptAmigo make your apartment hunt as easy as possible. Reach out and tell us about your lifestyle, budget, and amenity preferences, and our local experts will set up a day of tours to buildings you will love. The best part? It’s completely FREE.
* The original version of this article was first published on February 11, 2020.
Rebecca is a freelance writer over a decade of journalism experience. She graduated with a BA in Communications and a minor in journalism. She currently bartends in downtown Chicago and spends her free time exploring the city and making connections.
