The Haute Seeker

Kelli Haywood Shares the Coolest Neighborhoods for Running, Frites, and Fashionable Outfits in Chicago

Students at Dream Education program Founder Kelli Hayword featured on The Haute Seeker

In this week’s Seek Like a Local, Kelli Haywood, an award winning civic and non-profit leader shares her favorite places to run(and walk) in Chicago, where to find fancy fries on the South Side, and how her non-profit is exposing high achieving students to immersive and educational experiences across the city and beyond.

Explore Chicago Like Kelli Haywood

Kelli Haywood // Image provided by Kelli Haywood

Kelli Haywood is the Founder and Executive Director of Dream On Education, a Community Impact Manager for Cboe Global Markets, and the 2022 Nonprofit Civic Leader of the Year by the Executive Service Corps. In addition to Kellie’s civic work, she is currently an MBA Candidate at Emory University’s Goizueta Business School and a member of Delta Sigma Theta Sorority, Incorporated. Outside of work and school, Kelli enjoys running, cooking, and spending time with friends and family.

What’s a community organization that you support?

I’m a bit biased here! The non-profit that I support the most is my organization, Dream On Education. I founded Dream On about nine years ago. We provide academic, professional, and cultural enrichment services to high-achieving, low-income junior high students throughout the Greater Chicago Area.

Students at Dream Education program Founder Kelli Hayword featured on The Haute Seeker
Students from Dream on Education during an immersive experience // Image via Facebook

Each year, we provide our students with a wide variety of immersive, hands-on learning experiences, from culinary arts classes and entrepreneurship competitions to museum explorations and company visits (to name just a few). We take our youth on behind-the-scenes experiences to allow them to find academic, career and personal paths that excite and inspire them.

What is your favorite activity to do in Chicago?

My favorite thing to do in Chicago is to go for runs in different neighborhoods. Chicago has such a beautiful skyline and lots of really cool architecture. Going for runs or walks allows me to discover different areas to explore, cute coffee shops, restaurants to explore, and lots of really cool art. Some of my favorite places to run are downtown, on The West Loop, and along the lake.

Where is some of the best shopping in Chicago?

A store that I like a lot is Oak + Fort in Bucktown. I like clothes that are pretty simple but versatile – allowing me to wear them casually when I’m grabbing dinner with friends or dress them up a bit for work-related events. The colors are also pretty fun and clean, which I appreciate.

What are your favorite restaurants in Chicago?

I have two! For a delicious fast-casual meal, my go-to is Friistyle in Bronzeville. They have amazing Belgian-style pomme frites with a unique Chicago spin. My favorite is the Jerk Salmon frite, which is SO flavorful! 

Fries from Friistyle // Image via Facebook

When I’m in the mood for Italian, I go to Volare or Via Carducci. Volare has some black ink squid spaghetti—which may sound gross, I know but it’s delicious. Trust me!

Who are some of your favorite local artists?

A few artists that I like a lot are Julian “Logik” Gilliam, Diego Ross at Leaders1354, and Natalie Osborne. They each have their own style and use various mediums – from paint, spray paint, fashion designs, etc. Between the three of them, you’re bound to find some really cool pieces that inspire you!

Learn how you can support or get involved with Kelli’s non-profit Dream on Education by visiting their website at

Seek Like A Local, and discover things to do, places to dine, and more of what the city of Chicago has to offer this week. Check out more guides from influential Chicago locals at Seek Like a Local.

%d bloggers like this: