By: Ciara Suesberry
Chicago summers are famous for their energy — from rooftop brunches to festivals by the lake — but this year, something refreshingly new is docking on the shoreline.
On June 20, 2025, during the height of Black Yacht Weekend, the Play Hooky Experience is making its Chicago debut, bringing a day full of community connection, wellness, and pure, unapologetic joy.
Founded by Darryl “FollowtheDj” Dungee, a longtime advocate for mental health awareness and cultural celebration, Play Hooky is more than an event — it’s a national movement. Designed to encourage people to step away from the daily grind and reconnect with life’s lighter, more meaningful moments, the Experience invites Chicagoans to do something revolutionary: take a day to protect their peace.
Photo Courtesy: Darryl “FollowtheDj” Dungee
“Chicago knows how to show up for culture, community, and each other,” says Dungee. “Play Hooky isn’t about skipping out; it’s about showing up for yourself, your neighbors, and your joy. And there’s no better backdrop for that than Black Yacht Weekend.”
Set against the pulse of Chicago’s vibrant lakefront culture, the event will feature:
- Live music performances by local artists
- A curated vendor marketplace spotlighting Chicago creators
- Mental health and wellness resources designed for real community impact
- High-energy games and experiences for all ages
- Local food trucks and cultural eats
And in true Play Hooky spirit, the day isn’t about being flawless — it’s about being present. It’s about carving out space to celebrate achievements and simply being alive and connected in a city rich with creativity, resilience, and heart.
With roots in Baltimore and a national tour that’s stopping in cities like Los Angeles, Dallas, and Houston, Darryl’s Play Hooky Experience reflects a broader movement toward intentional living — one that especially resonates in urban spaces where hustle culture can often eclipse the need for rest, reflection, and joy.
For Chicago locals, it’s more than an event; it’s a call to prioritize wellness without giving up the vibrant city life they love. Whether coming off a yacht cruise or stepping away from the boardroom, Play Hooky offers a space where community and culture take center stage.
Because in a city that moves as fast and fiercely as Chicago, sometimes the powerful thing you can do is simply pause, play, and reconnect.
Event Details:
Play Hooky Chicago
Date: June 20, 2025
Location: 838 West Kinzie Street, Chicago, IL
Open to the Public | Family-Friendly | Local Vendor Marketplace
Highlights:
- Local Music & Live Performances
- Vendor Village Featuring Chicago Entrepreneurs
- Mental Wellness Workshops and Activations
- Cultural Food and Community Connections
About Play Hooky Experience:
The Play Hooky Experience is a national movement founded by Darryl “FollowtheDj” Dungee to promote mental health, community connection, and cultural joy through experiential events. With a heart for healing and a beat that unites, Play Hooky is redefining how we gather — one city at a time.
Follow along at @FollowTheDJ and @ThePlayHookyExperience for updates and announcements.
For interviews or media inquiries:
Berry Dynamic Agency
Launch@berrydynamicagency.com
Published by Jeremy S.
