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Sat, Sep 30



Summer of Dreams

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Summer of Dreams
Summer of Dreams

Time & Location

Sep 30, 2023, 5:30 PM – 11:00 PM

Chicago, 1339 S Wood St Suite A, Chicago, IL 60608, USA

About the Event

A Boy & His Dream - Summer of Dreams

Saturday, September 30, 2023

We are very excited to announce A Boy & His Dream is hosting our ‘Summer of Dreams’ event, a fundraiser for underserved youth. A Summer of Dreams will be held on Saturday, September 30th, beginning at 5:30 PM.

This special event will be held at Vertiport Chicago. The night's highlight is an exquisite fashion show featuring designers with African inspiration crafted into each piece, exciting the audience to raise money for underserved youth. In addition to this unique fashion show, there will be local vendors, DJ Apollo and Bowlbay spinning beats to light up the night, a silent auction, and VIP Helicopter experiences. 

Delicious local featured Hors-d’oeuvres, refreshing cocktails, and wine from our amazing sponsors will also be key parts of the evening and included in your ticket purchase.

With your generosity, we hope to raise $100,000, which will allow us to provide playgrounds to underprivileged children in Nigeria as well as towards scholarships for our brilliant students of Chicago to greater their education & future.


A Boy and His Dream was founded in 2015 by Sunny Akhigbe - someone who has lived and walked the devastation of opposition, adversity, and a troubled beginning. Since then, he & his growing team have created programs that generate change in the youth who are our leaders of tomorrow. A Boy and His Dream is a 501(c)(3) charitable organization that supports underserved youth. They focus their charitable giving on two pillars: Underserved Youth in Chicago and Underserved Youth in Nigeria.


A Boy & A Dream’s mission is to provide opportunities to underserved youth while giving back to its communities.


A Boy & His Dream believes every child has the right to play and physical activity is critical to a child’s development and directly correlates to how they perform in the classroom.

For the underserved schoolchildren in Nigeria, they build playgrounds, provide educational sessions, and deliver meals, school supplies, and toys. In March, they built a playground and delivered 50,000 meals, stuffed animals, and school supplies to the schoolchildren in the village of Ekpoma, Nigeria. Here is a link to the recap of the mission trip in March.

Our goal over the next 5 years is to:

  • Build 100 playgrounds
  • Deliver 1,000,000 meals
  • Educate schoolchildren
  • Offer work programs
  • Supply schools with school supplies and toys

For the underserved youth in Chicago, they offer a scholarship program where we provide scholarship money for their college education and direct 1:1 mentorship.

The goal over the next 5 years is to:

  • award over 100 student scholarships
  • mentor all students in the A Boy and His Dream scholarship program
  • provide more connections for our students via national and global networks
Hosted By Ryan Chiaverini

Ryan Chiaverini is a Chicago/Midwest Emmy Award-winning television personality, actor, musician, and co-host of Windy City Weekend, formerly Windy City Live on ABC7 Chicago (WLS-TV) alongside Val Warner.  Formerly the sports anchor for ABC 7's top-rated weekend newscasts, Chiaverini auditioned for Windy City LIVE and was chosen for the top co-host job from a field of several hundred candidates. His charm and ease as an interviewer were first noticed when he hosted ABC 7's Bears' pre-game show, THE CHICAGO HUDDLE. Ryan's quick wit, work ethic, and reputation as someone you can't help but like, made him the perfect choice for ABC 7's new local show. Ryan's trademark "2-Minute Warning" segments, featuring entertainment and sports celebrities answering fun trivia questions, has become a Windy City LIVE favorite. Chiaverini has interviewed some of the biggest names in entertainment, sports and music including Will Ferrell, Jimmy Kimmel, Jane Lynch, Bonnie Hunt, Mike Tyson, Chance the Rapper, Barry Manilow, Patrick Kane, Kerry Woods and Joe Maddon. Prior to Windy City LIVE, Chiaverini joined Chicago's Number One sports team as sports reporter/fill-in anchor in March, 2006 was promoted to sports anchor on the station's weekend newscasts.

Featuring Jay Deep

Jay Deep is a native of Chicago, who became a favorite performer throughout the Midwest & abroad.After bursting on the comedy scene in the mid 90's. He's performed in cities such as Las Vegas, New York, Miami; as well as internationally in Amsterdam, Belgium,Rotterdam, London, Montreal and Toronto to name a few.

His success in stand-up comedy brought Hollywood knocking, landing him cameos in films such as Paramount's “Light It Up”, MGM Pictures “Barbershop”and “Barbershop2: Back in Business”. His television highlights include eight seasons of BET's“ComicView” plus a half hour comedy special.He also performed on HBO's “Bad Boys of Comedy” and has a 5-star rated, Amazon Prime comedy special, “Ain’tIsh Shy About the Chi.” He’s as comfortable in front of the camera as he is behind the scenes. Graduating from the New York Film Academy, he took the knowledge he learned & applied it, by most recently directing two short films,  “The 40+Double Dutch Club – Beyond the Ropes” and basketball documentary“Ball Like Me”. The opportunity was presented to him to share what he’d learned about the industry by teaching Improv and Theater in the Summer Internship for the Gifted at the University of Chicago — he took up the challenge and excelled. This landed him another opportunity to teach creative writing to students in the ARTINC program in Peoria, Illinois.

Jay currently resides in Chicago and believes, “Success is not to be pursued; it isto be attracted by the person we become.”

Thank you, Sponsors!

Adalina Chicago

Glengarry Scotch Whisky

Obulu Coffee

Riboli Family Wines

Tequila 1349

Vertiport Chicago

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