Children are the legacy of every community—and when we invest in their dreams, we build a future filled with possibility.

A Boy and His Dream Annual Legacy Gala

Saturday, February 21, 2026

6 PM - 10 PM

Midland Hotel 🏨 

Downtown Chicago 🏙

This magical evening, hosted by Samantha Chatman and Ryan Chiaverini of ABC 7 Chicago, will celebrate the power of hope, community, and collective impact.

Extraordinary live performances by international artist, Ivanna Melay and The Yohan Experience.

Why This Legacy Gala Matters More Than Ever

Your generosity has turned dreams into action.

• In Chicago, we’ve now awarded scholarships to over 75 students, providing not just financial support, but also mentorship, professional connections, and a belief in what’s possible.
• Last November, 4 new playgrounds will be built in Ekpon, Nigeria, offering joy, safety, and belonging to thousands of children.
• Together, we've delivered thousands of meals, stuffed animals, school supplies, and hygiene essentials to underserved youth—reaching thousands of children with love and care.

This growth is because of you. And we're just getting started.

The Legacy Gala goal is to raise $100,000 to expand our reach—supporting more students in Chicago and building more educational and play spaces for children in Nigeria.

Purchase your tickets today and be part of something truly special.

Tickets Available Here!

The evening will captivate you with the following:

✔ Welcome Reception

✔ Exquisite 3-Course Seated Dinner

✔ Silent & Live Auctions by renowned auctioneer, Big Mike

✔ Live Entertainment by The Yohan Experience & Ivanna Melay

✔Special Guest Speaker, A Boy and His Dream Scholarship Recipient, Loyal Bridges

✔Art Gallery featuring global artists Joanna Cislak & Peter Blindt

(A portion of all art sales will benefit A Boy and His Dream)

✔After Party at TAO Chicago

and More!

Be part of an unforgettable evening—and a legacy that lives on in every child we serve.

Thank you to all of our previous and current sponsors for making The Legacy Gala happen! 

A Boy and His Dream is a volunteer-led 501(c)(3) organization. Every dollar raised directly supports underserved youth in the U.S. and Nigeria.

For Chicago youth, your support provides scholarships, mentorship, and life-changing opportunity.
For Nigerian youth, your support builds playgrounds, provides meals, stuffed animals, school supplies, and opens doors to learning.

Together, we are shaping futures.