Kaina Castillo Steps to the Front of the Stage

Age: 20  Neighborhood: Irving Park • Follow: Twitter // Soundcloud


The beautiful thing about Chicago as a creative outlet has always been the affordability it allows while interacting in a locale on par with Los Angeles or New York City. Lower rent and less people means a bit more room to move around, be creative and grow into one’s destined medium. There’s room to move around and explore and no one knows that better than 20-year-old singer/do-everything Kaina Castillo who has been making a name for herself around the city through a series of hustles that have only begun to find their way to the public. 

The Depaul student splits her time between a variety of hustles that have all individually contributed to her own personal creative journey. Taking advantage of her time in school, she took up Public Relations and Advertising, strategic majors that should pay off after graduation.

“I currently really hate school,” said Castillo laughing. “It’s hard for me because I was born and raised in Chicago and have been doing a lot of the things I want to be doing since high school so sometimes it feels like school is holding me back from the things I want to do. I’m gonna try to find the silver lining to college – hopefully to build an audience for whatever work I’m doing.”

That silver lining seems to be shining brightly as a series of endeavors have found the young artist work her way into several experiences have at once served as a chance to learn and an opportunity to progress professionally. Working with our September 2015 cover story The O’My’s, Castillo has helped to run social media, create and execute a brand and deal with the more mundanities of the music industry that many in a typical college class may not come across, a sentiment that was underlined during her work with the marketing team at Bucketfeet where she served an internship.

With all of that going on, Kai has still found time to craft a music career for herself. Popping up on stages all over town as part of a series of endeavors that include The Happiness Club, “a group of kids from ages like 5 to 21 that create their own original content which includes poetry, dance, singing, rapping, etc. to promote positive values within youth and our community.” She has performed at Lollapalooza and The White House on several occasions.

As of late, she has begun to find her voice, making a welcome guest feature on Noah Sims’ recent Testament project and beginning to record new music with the likes of The O’My’s Boyang Matsopola and her band which she describes as a blues-y sort of trap sound (shout out Netherfriends).

Regardless of the path she follows, Kaina has set herself on a solid approach moving forward and we at TheseDays are excited to see what she has in store on her debut project, due out later this year.

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