0

Check Out Our 7 Favorite Street Artists Based in Chicago

Chicago-Street-Artists

The Art Institute of Chicago is world famous for providing the city with a wealth of art and culture. But there is one group of artists that you might have overlooked: Chicago street artists.

Chicago has a bit of a rocky history when it comes to street art. But today there’s a host of talented Chicago-based street artists that are challenging our perceptions of what art can be.

We’ve created a list of 7  street artists that are making a lasting impact on the city. We chose these street artists based on several factors:

  • Their distinct art style
  • The size and prominence of their street art
  • The level of recognition and influence they have in the street art scene

Check out our list and discover some of the most talented and recognized Chicago street artists

Top Chicago Street Artists

There are plenty of city neighborhoods to see Chicago’s street art scene and Chicago-based artists. We should know, we named one of our bags after them.

For instance, the Wells Street Art Festival, held each June in Old Town, brings in more than 200 artists from around the country and raises money for community causes. Hyde Park has also been hosting the 57th Street Art Fair each June for 70 years.

These are opportunities for local and national artists to show off their art where the community can appreciate it.

But the beauty of street art is that you don’t need a festival or venue to view the art. The city is their canvas. So the next time you’re bustling around the city be on the lookout for some of the Chicago street artists that made our list.

1. JC Rivera

Few images in Chicago’s street art scene are as instantly recognizable as JC Rivera’s “Bear Champ.” This enormous bright yellow bear appears in a variety of street murals throughout the city.

The bear seems cute and cuddly at first, but also projects a bit of a rugged, streetwise vibe — the perfect representation for life in Chicago.  Rivera has been painting in and around Chicago for a decade. His work is most known for its bright, colorful and uncluttered look.

All done with this one.

A photo posted by Jc Rivera (@jcrivera) on

Rivera doesn’t just produce street art – he also has created Bear Champ-themed shoes, vinyl figures, and even custom-designed refrigerators.

You also don’t have to wander through the city to see his work – like many artists, he also displays much of his skill online and on social media. Of course, a real-life viewing experience can’t be beat.

2. Hebru Brantley


As a child growing up on Chicago’s Southside, Hebru Brantley started his artistic endeavors by tagging. But he soon discovered the fun in creating more intricate designs and telling stories through the heroic characters in his artwork.

For a young kid in the inner city, walking into a museum becomes daunting …So if I can be the start to get the next generation to start to look at work in a different way and make it more approachable, to me that’s everything. – Hebru Brantley, Billboard Art Basel Interview

His artwork has a bit of a comic book feel, with some characters, like the goggled Flyboy, often depicted soaring through space.

Blk Grl Fly

A photo posted by Hebru Brantley (@hebrubrantley) on

Brantley’s art has been featured on many Chicago wall murals plus more than a dozen galleries from coast to coast and even a few shows in Europe.

Famous celebs like Jay-Z and other musicians prize pieces from Brantley, and his social media accounts often feature many of his inspiring creations.

3. Don’t Fret

Look in the mirror #dontfret #dontfretart #chicagoart #chicago #wheatpaste #pasteup

A photo posted by Dont Fret (@dontfretart) on


Don’t Fret’s images could definitely be called cartoony, even childish. Some even give off the impression that a teen came up and scrawled silly thoughts, dorky puns and primitive drawings on a wall.

But don’t be fooled. Of course,  there’s plenty of skill and experience involved in Don’t Fret’s street art.

It’s a good day for some Paletas… #dontfret #dontfretart #chicago #wheatpaste #pasteup #logansquare

A photo posted by Dont Fret (@dontfretart) on


In past interviews he’s said he likes sharing messages that aren’t serious and make people laugh. While his pieces do possess comical elements, they also serve as snapshots of life in the city.

His Chicago murals and other artwork can most commonly be found near many of the city’s neighborhood dive bars, which Don’t Fret believes have a special and important vibe.

4. Pizza in the Rain


While some Chicago street art scenes are bursting with color, the creations by Pizza in the Rain are stark and minimal. This lack of  color only makes them stand out more.

The artist known as PITR creates original black-and-white paintings with long lines and sharp angles. He also incorporates wheatpastes, a kind of liquid adhesive that adds an extra texture to his street artwork.


In addition to creating and promoting his own artwork, PITR finds ways to collaborate with other street artists. Recently, he invited his peers to create a series of over-sized black-and-white panels displayed throughout the downtown area.

Named the White Wood Project, him and his fellow street artists displayed these panels without property owner’s permission. While some pieces disappeared quickly, some property owners appreciated the artwork and kept it up.

Pizza in the Rain’s artwork can also be found in galleries, but unlike some artists who don’t mind  their identities being public,  PITR prefers his anonymity.

5. Sentrock

A little throwback piece✨ STAY FLY & blessed 🙏🏽( @saint.tiger 📸📸 )

A photo posted by @sentrock on

Joseph Perez, who goes by the tag “Sentrock” is definitely one of the area’s  more famous street painters.  His work is featured throughout the city, including indoor and outdoor walls, and a variety of local galleries.

Sentrock’s pieces center around the overall themes of hope and empowerment. He expresses these themes most notably through his depictions of his “bird boy” caricature.


While some street artists have honed their craft through trial and error, Sentrock had formal art training in Arizona. He was also the winner of a “Big Brain” award for innovation.

However, he has said he prefers the freedom of expression available in Chicago. Like many of his peers, Sentrock built up his street art cred by tagging, and then went on to create larger murals.

He also teaches art at Chicago schools. These days, his work appears on  murals in Chicago but he sometimes returns to Phoenix to display his art and create murals – even custom shoes.

6. Max Sansing

Ororo Munroe in progress. 📷 @jeff_mancilla_ #stormisbrewing #tchallaiscoming #maxsansing

A photo posted by Max Sansing (@maxsansing) on


A native of Chicago’s Southside, Sansing taught himself oil painting and began his street art adventures with basic graffiti and tagging as early as the mid-90s.

He continues to perfect his skills and received formal art training from the American Academy of Art.

Sansing’s initial area of work was the Hyde Park/Avalon Park areas, where he was part of the area’s hip-hop culture.

#maxsansing #hebru #KrisBryant #publicartchi

A photo posted by Chicago Truborn [Gallery] (@chicagotruborn) on


He and his peers perfected their artistic skills on various buildings and he has earned a reputation for realistic portraits and bright colors. Sometimes he would draw highly detailed human faces but add swatches of color to make them stand out even more.

Today, he enjoys working with new street artists, and believes that investing in art and creativity and making new murals can inspire them to resist the temptations and destructive paths of the area’s gang and drug scene.

7. Bunny!XLV


The Chicago-based artist with the cryptic-sounding name loves imperfections and shows it off in his art. His works, while not always life-like, are especially expressive and colorful.

Many have said his pieces belong in a world created by Tim Burton, such as nearly abstract human figures bursting with color. Bunny is also big into drawing animals, the more imaginative the better. Originally from Costa Rica, he is known for his colorful freehand work on a variety of Chicago murals.

Morning walks back home and still riding #bunnyxlv #streetartchicago #wheatpaste

A photo posted by Bunny XLV (@bunnyxlv) on


In addition to honing his craft on Chicago’s streets, the artist with one of the most clever street artist names received comprehensive art training from the Art Institute of Chicago, in everything from screen printing to pre-press.

He and fellow artist Simone Garcia created a “street art-only” gallery that not only shows the area’s talent but also tells a story.

Final Thoughts

Despite the city’s mixed feelings about the artistic value of street art, the city is home to many inspiring street artists that are leaving their mark on this urban jungle.

Next time you’re walking through the city, look up from your phone and take a second to appreciate the many murals that are featured on buildings across Chicago. You might even start to recognize certain artists and see pieces completed by the talented artists from our list

Have you noticed any street art on your commute through the city? Leave a comment below and tell us your favorite piece of street art and where we can check it out!

Meghan Ward

Leave a Reply

Your email address will not be published. Required fields are marked *