In search of opportunity, some young South and West siders are turning hobbies into side hustles, building skills for possible careers and leveraging personal connections.
By Hector Cervantes, Robyn Meurkson, Robert Speed and Leona Towner
Davonte Cole, age 14, and Messiah Williams, age 16 (right) layout heat press designs for t-shirts during Crushers Club in Englewood on Monday, July 14, 2025. (Talia Sprague/for City Bureau)
What young people do in the summer has remained a frequent source of debate in Chicago, as local officials pushed a controversial “snap” curfew to prevent so-called teen takeovers, and young people look for third spaces and activities to hang out with their peers.
But for some of Chicago’s young people, work is top of mind.
Students and young people in Hyde Park, Kenwood and Chinatown shared their experiences with City Bureau’s Civic Reporting fellows in May about summer employment, safety and available job opportunities.
Some are tapping into family connections and approaching businesses directly rather than waiting for summer job opportunities to come to them. Those conversations showed a disconnect between the city's One Summer Chicago program — which employed 27,793 youth in 2024 and aims to employ nearly 29,000 in 2025 — and young people trying to find work. Personal relationships often provided opportunities that formal programs couldn’t match, students said.
Others are using their hobbies and educational opportunities to plan the next steps in their careers and interests. They, too, emphasized leveraging personal relationships and following their passions to achieve their ambitions.
This comes amid broader conversations in recent years about youth unemployment and discontinued education, which disproportionately affects Black and Latino youths, and those in South and West Side neighborhoods, research shows. Unemployment rates in Chicago for Black adults ages 20 to 24 rose in 2023, while it fell for other demographics.
These interviews have been edited and condensed for clarity.
Kenwood Academy High School
Kenwood Academy High School sits in the center of a busy food and recreational commerce area, making it a great place for the school’s open lunch policy (and a better place for after-school snack destinations). A block away from the school, you can find Domino’s, Whole Foods Market, McDonald’s and Uncle Joe’s Jerk Chicken before the community opens into the active Hyde Park neighborhood full of bookstores, hairdressers and gyms.
Amira Jackson, 17, is a Kenwood Academy junior who worked last year for her cousin’s coffee shop, Erin’s Cup — an organization that partners with One Summer Chicago to employ youth.
WHAT ARE YOU DOING THIS SUMMER?
I'm doing something new: boxing. I'm a sales associate. I actually just came from the interview, like, just now.
HOW DID YOU HEAR ABOUT YOUR JOB?
I was looking on Indeed. And I used to do boxing when I was younger. So I looked up a lot of mental health and fitness, you know, wellness places, and I looked up Rumble Boxing, and I saw them on TikTok. I was like, this is so cool and a lot of women go there.
WHY DID YOU CHANGE JOBS?
[At my One Summer Chicago job], it was like $15 or $16 an hour. But then I started working at Walmart, and that was $17 an hour, and after seeing those checks, I just couldn't go under that.
(L-R) Mya and Keelani Williams, and Nikea Harris pose for a picture outside Kenwood Academy High School.
Nikea Harris, 18, is a senior at Kenwood Academy who secured two summer jobs through different paths. He plans to study law in college.
How did you find your summer jobs?
I plan to work for the Golden Apple [restaurant in Lakeview], and I also have a job at [Raising] Cane’s. For Golden Apple, it came through from the school, so my teacher recommended me, and for Cane’s, I just applied, and they emailed me out of nowhere, and I got the job.
Have you heard of One Summer Chicago, and what was your experience applying?
I did fill out an application, but they didn't end up getting back to me. I'm not sure why. Maybe I gave them the wrong email. I'm not sure what really happened.
If you had one thing to tell leaders about youth and employment, what would it be?
I would ask them, why did they choose their profession, how did they come about it, and do they really enjoy it?
One thing I probably would say to them is just be open-minded to teenagers.
What do you think about the ‘teen takeovers’ that have been in the news?
I feel like that's just certain groups. Not all teenagers are like that. So I feel like they should still give each teenager a chance to redeem themselves. You’ve got to give them a chance before they do something wrong first.
Kosi Martin, 17, is a Kenwood Academy student going into his second year of the University of Chicago youth internship summer program. He said it's short enough to get him paid and give him enough free time to enjoy summer.
HOW DID YOU FIND OUT ABOUT YOUR SUMMER PROGRAM?
My parents introduced me to the program last year, and then for this year, I’ve just been introducing it to friends, and they've been telling others to do it, as well.
HOW HAVE YOUR SUMMER PROGRAMS CHANGED OVER THE YEAR?
I did One Summer Chicago a couple years back, so the experience is different.
With One Summer Chicago, I was just getting a stipend. So the big difference is probably just money.
When I started doing the UChicago program at 16, I was getting paid minimum wage. UChicago does give more money [than One Summer Chicago], and it pays me for 20 hours per week.
WHAT SHOULD PEOPLE IN CHICAGO KNOW ABOUT WHAT TEENAGERS WILL BE DOING THIS SUMMER?
I think they should probably be aware of where teenagers could be at because sometimes teen takeovers are seen to be unsafe, and it could be dangerous at times, but practice being aware of where they’re going, so that you know where to avoid.
Hyde Park Boulevard and Lake Park Avenue
The busy intersection of Hyde Park Boulevard and Lake Park Avenue serves as a transit hub where quick conversations about employment and summer plans can happen between bus arrivals. Kenwood High students, University of Chicago students, and residents hurry to catch buses that connect them to jobs and activities across the South Side.
Dante Stewart, 24, has been working at Whole Foods Market in Hyde Park full-time for four years. He works a 4-10 p.m. shift throughout the week — but has other plans to make money this summer.
WHAT ARE YOU DOING THIS SUMMER?
I got lots of paid time off saved up. I am getting into streaming, like Twitch streaming. So, I've been getting everything I need to be able to do that. I want to go around different places and do [In Real Life] IRL content. I want to do that all summer and have a financial goal I am trying to reach.
HAVE YOU HEARD OF ONE SUMMER CHICAGO?
Yea. I participated in it when I was younger. I changed summer jobs while doing it, but honestly I was just doing it for the money. One Summer Chicago got me through [the summer]. I encourage everyone to do it, or just to do something with themselves [to keep busy].
Ping Tom Park
Located in the heart of Chinatown, Ping Tom Memorial Park is a 17-acre urban oasis that offers scenic views and community gathering spaces. Named for Chinatown’s most prominent civic leader, the Chicago Park District began transforming the former rail yard along the Chicago River in 1998.
Kayla Medina, 26, of Pilsen, graduated this spring with a master’s degree in elementary education from DePaul University. She was taking graduation photos at the park. Medina participated in the Academy for Urban School Leadership program. The AmeriCorps funding cuts stopped her biweekly payments in April and eliminated her $6,000 end-of-year stipend, leaving her unpaid for the final months of her year-long teaching residency. It’s unclear whether two recent federal rulings could result in her getting paid.
Kayla Medina, 26, poses for a photo at Ping Tom Park where she was taking pictures to celebrate her graduation from DePaul University.
What are you looking forward to doing this summer?
I plan to get my [English as a Second Language] endorsement, because I’m going to be working at Orozco Community Academy, which has a bilingual fine arts gifted program.
Do you think DePaul prepared you for the future as you enter the adult world?
While I don’t think DePaul necessarily prepared me, the AUSL program I did absolutely did. It's funded through AmeriCorps. Right now they did just get a lot of cuts to educational funding, but AmeriCorps does technically run it still.
You work with a teacher in a classroom. I was in a third-grade math and science classroom at Marquette Elementary School for a year. I basically was just teaching and trying a bunch of strategies on how to become a teacher and educator.
What is your advice for young Chicagoans?
Follow your dreams, even though it feels like you can't right now. Really strive for what you want to be and have a passion towards it.
Amare Saunders, 18, from Humboldt Park, is an avid photographer who will attend the University of Wisconsin-Madison in the fall.
What do you do for fun?
I do photography. It's very fun. I get a lot of different perspectives and just get to capture moments in still spots. I enjoy that. I met my mentor about a year ago. Before I knew anything about photography, I tried it out with him and I liked it.
tell us more about the photography work you’ve done.
I do it mainly as a hobby, but I also do side gigs occasionally. I do different events in the neighborhood, like in North Lawndale. I do shoots for them and for a local church around the North Lawndale area, and individual shoots as well, like for people going to prom.
What advice would you give to youth trying to grow and develop their skills?
I would say just talk to as many people as possible and get connections. Your connections are where everything stems from, because if you're unknown, then you don't even have a platform to share what you could do.
Support City Bureau’s Civic Reporting fellowship by becoming a recurring donor.
Check back later this summer to see more of our fellows’ work on youth and summer opportunity.