'Windy City Weekend' talks back-to-school; singer Brooklyn Dylan performs latest single

ByABC7 Chicago Digital Team WLS logo
Friday, August 14, 2026 7:11PM
Windy City Weekend - August 14, 2026

CHICAGO (WLS) -- A new school year brings new teachers, new opportunities and new beginnings.

Making the transition a little easier for local families is a familiar face of the show, Dr. Aleta Clark, better known as "Englewood Barbie," with CEO of BigHeart Health, Cheryle Jackson.

They joined Val Warner and Ryan Chiaverini to discuss the Hugs No Slugs Back-to-School Drive.

This year's drive is bigger and better than ever. The event will take place from noon to 4 p.m. Saturday at Englewood STEM High School and will feature special guest Mayor Brandon Johnson, who will speak directly to children and families in attendance.

For more than a decade, her organization has supported the community with valuable resources, including free haircuts, dental cleanings, life insurance information and much more.

Hear more about what she had to share for this year's event.

Almost 10 years ago, Raven Smith came on "Windy City" to promote the work she was doing at just 17. Fast forward and the Chicago native is back again with some exciting news about her third installment of her Raeted R Creative Co. fashion series. This year's theme is "Rouge," exploring punk and alternative fashion. It brings storytelling, fashion and art together. The event will take place at the Epiphany Center of the Arts on Saturday.

Couponology is also in their back-to-school mode and has the deals you need to head into the new school year in style.

Duluth Trading Company

Go back to the classroom in style with Duluth Trading Company's apparel. The Heritage Wide Jeans and Women's COOLMAX Chambray Shirt offer an easy, versatile look, while the Fire Hose HD Commuter Lunchbox keeps meals fresh on the go.

Get 20% Off Your Order of $100 or more with code WIND20

CookUnity

Weeknight dinners just got a whole lot easier and fresher with CookUnity's chef-crafted meals delivered right to your door. This chef-driven meal delivery service offers meals from 130+ top chefs, including Michelin-starred talent and James Bear Award winners.

Save 50% off your first week, 10% off the next three weeks with code SCHOOL50

COURSERA

Learn new skills and explore the world of artificial intelligence from the top universities and companies. Coursera offers tailored courses for continued education and so much more: 40% on three months of unlimited access with a Coursera Plus subscription.

RAG & BONE

There's some more room to upgrade your wardrobe with Rag & Bone's Collegiate Collection. Featured styles include the viral Miramar Sport Stripe Track Pant, giving you a comfortable, chic look.

Get 20% Off Sitewide with code WINDYCITY

Brooklyn Dylan stopped by the "Windy City Weekend" studio to perform her latest single, "Ghost." This emotional pop-rock anthem explores the memories that linger after a heartbreak.

At just 17, the singer, songwriter and musician has already achieved remarkable success. In 2022, Dylan was named Powerhouse Music Artist of the Year, and at 14, she released her debut single, "How the Story Ends."

Her breakout hit, "Bad Blood," marked a major turning point in her career, reaching No. 1 on Top 40 radio, while the music video reached more than 1.7 million views.

Dylan's debut EP, "Mascara Confessions," drops this fall.

For more information, visit brooklyndylan.com.

Copyright © 2026 WLS-TV. All Rights Reserved.