Season to Soar

07/24/2026

We are incredibly honored and grateful to The Chicago Community Trust Young Leaders Fund, an initiative of The Chicago Community Trust for awarding Season to Soar a grant.

Thank you for believing in our mission and investing in the future of our communities and our youth.

We are eager to continue uplifting underserved communities and developing the next generation into leaders with servant hearts and global perspectives.

It was also a pleasure meeting with Carrie Goodale yesterday and learning more about the incredible work that the Chicago Community Trust and its affinity groups are leading to create a stronger, more equitable Chicago. We are inspired by your commitment to community and are excited about the opportunity to build a lasting partnership with the Trust.

We look forward to creating meaningful impact together for years to come.

https://www.cct.org/stories/young-leaders-fund-awards-105000-in-its-2026-grantmaking-cycle/

Young Leaders Fund (YLF), an initiative of The Chicago Community Trust, has been paving the way for start-up nonprofits and the next generation of philanthropists…

07/04/2026

Happy Fourth of July from Season To Soar! Today, as we celebrate alongside our neighbors and friends, we are reminded of the power of community and the boundless potential within every young person. Enjoy the parades, the fireworks, and the time spent with loved ones today.

Stay safe, and keep soaring! 🦅🇺🇸

06/26/2026

Chicago youth, this one is for you!

Season to Soar is offering a special opportunity for young leaders to engage in leadership development within a historic new space designed to inspire hope, foster community, strengthen leadership, and activate the power of change.

The museum is already booked out months in advance, so don’t wait.

Fill out the quick form here to be considered:

https://docs.google.com/forms/d/e/1FAIpQLScxdD_qufF2_nHKJgQo1TXwwah4NuFotlu38SC5IlqOzIGXug/viewform

Please share with a young person, parent, mentor, educator, or community leader who should see this.

Obama Foundation Chicago Public Schools

06/24/2026

As ABC 7 Chicago highlights, Season to Soar hosted a youth-centered conversation on “teen takeovers,” bringing young people together to speak on safety, accountability, and the impact of social media on these gatherings.

06/21/2026

To the dads, granddads, uncles, and mentors who lift us up and teach us how to fly, thank you!

06/19/2026

Honoring the past. Celebrating freedom. Empowering the future.

Happy Juneteenth!

06/02/2026

One of the most impactful parts of NBC News coverage never made it on air.

NBC Chicago came out to feature Season to Soar and KCC Academy’s work uplifting youth voices and addressing concerns around teen takeovers and youth trends. The story highlighted meaningful efforts from both organizations and gave young people a platform to share their perspectives.

But after the cameras stopped rolling, the impact continued.

What viewers didn’t see on camera was just as powerful. Reporter took the time to connect with youth in a genuine and engaging way by simply inviting them to ask him questions.

The students curiously and excitedly asked Randy question after question from what it’s like to be a reporter, to whether he would attend an “adult takeover” if one happened. (That one fried me lol)

Just by taking the time to engage with the youth, he created a meaningful and impactful moment. His willingness to engage openly, listen, and share his experiences provided them with insight into journalism, the news industry, and exposure to career pathways they may never have considered otherwise…and trust me, their answers to his original interview questions were on point, so I know that now that they see the possibilities, we might really have some future reporters in there :)

We are grateful to NBC Chicago not only for shining a spotlight on the work of Season to Soar and KCC Academy, but also for investing directly in our young people.

Thank you for helping amplify youth voices and for demonstrating what meaningful community engagement looks like. Experiences like this are ones that our youth will remember forever.

Thank you, Randy and NBC Chicago, for being a true community partner. We appreciate you!

Randy Gyllenhaal

05/31/2026

A huge thank you to NBC Chicago for covering Season to Soar and KCC Academy's work connecting with youth, reinforcing servant leadership, and promoting civic engagement at a time when teen trends and takeovers are on the rise and promoting positive values is needed most.

NBC NBC News

A “teen takeover” was seen at a Chicago beach late Friday as concerns rose about such gatherings escalating into violence. Randy Gyllenhaal reports.

05/31/2026

We are grateful for CBS Chicago's coverage that highlighted Season to Soar and KCC Academy's "Inside Takeover & Trends," a powerful conversation where youth shared their insights and perspectives on recent teen takeovers and trends.

We’re grateful for the platform and support in amplifying youth led dialogue.

We look forward to continuing to create spaces where young people lead the conversation and drive change.

Check out the full interview linked below.

https://www.cbsnews.com/chicago/news/teen-takeovers-conversation-south-side-discussion/

CBS News CBS

05/28/2026

Thank you to ABC 7 Chicago for covering tonight’s “Inside Chicago Teen Takeovers” conversation hosted by Season to Soar. ❤️

This youth-led community conversation was created to give young people space to speak for themselves about issues often discussed around them, including safety, accountability, social media influence, community impact, and solutions.

We believe real change starts with listening.

📍 460 E 75th St, Chicago, IL
⏰ Tonight | 5:00 PM to 6:00 PM CT

Read the story here:
https://abc7chicago.com/post/community-organization-season-soar-hosting-youth-centered-conversation-teen-takeovers-chicagos-south-side/19187556/