Cultivating curiosity, courage, and character.
"Empowering young minds to lead, learn, and live with purpose."
At Dream Big Mentoring and Outreach, we believe that every child deserves consistent guidance, positive role models, and opportunities that empower them to rise above their circumstances. Our Mentoring Program provides a structured, compassionate alternative for youth who need encouragement, direction, and meaningful connection.
We proudly serve students ages 5 to 17 in the Greater Grand Crossing, Chatham, Englewood, Woodlawn, South Shore, and Back of the Yards communities.
Through a network of trained mentors, educators, and social service professionals, Dream Big delivers a comprehensive range of programs designed to foster personal growth and lifelong success.
To ensure a holistic approach, Dream Big collaborates with a dedicated network of social workers, counselors, and therapists who provide individualized support to both students and their families.
These include:
Key focus areas include: Job readiness and career exploration Tutoring and Small Group Collaboration AfterSchool Programming/Arts And Crafts Academic improvement and educational success Financial management and decision-making skills Positive social interactions and leadership development Mental and emotional health awareness All Dream Big mentors and staff undergo extensive training and background checks to ensure the safety and well-being of every student. Each program year begins with a Kick-Off Celebration to welcome new participants and foster a sense of belonging and excitement for the journey ahead.
Before becoming an official 501(c)(3) nonprofit organization, Dream Big operated informally for more than seven years, serving over 500 boys and girls throughout Chicago’s South Side. Many of these students entered the program performing two to three grade levels behind, yet through the dedication of our volunteers and educators, we successfully developed individualized plans to help every student reach — and often exceed — grade-level proficiency.
Today, our structured mentoring model continues this legacy of excellence. Students meet with mentors and staff for approximately 20 hours per week over a 12-month period, engaging in activities centered around goal setting, academic support, and personal development. Mentors motivate students through positive reinforcement, recognition of achievements, and celebrations of progress.
Our Impact and Commitment
At Dream Big, we understand that true transformation begins with the entire family. That’s why our program offers family engagement sessions to strengthen relationships between parents, students, and schools. We provide guidance on how families can effectively support their children’s academic and personal development.
On a monthly or bi-monthly basis, we also invite professionals from our network of social workers and mental health experts to host presentations and activities for students and parents. These sessions not only offer valuable resources but also work to eliminate the stigma surrounding mental health support in our communities.
Dream Big believes in expanding horizons. Our monthly or bi-monthly field trips allow students to explore Chicago and experience opportunities beyond their immediate neighborhoods. From visits to colleges and museums to cultural and professional institutions, these outings serve as both educational enrichment and motivational incentives for continued growth.
To ensure the success of our initiatives, Dream Big uses evidence-based assessment tools, including the STEP Literacy Assessment, developed by the University of Chicago Urban Education Institute. Our structured evaluation process includes:
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Assessing student needs and identifying goals
-
Conducting instructional and environmental analysis
-
Developing customized learning and mentoring strategies
-
Creating and revising instructional materials
-
Conducting formative and summative evaluations
This ongoing evaluation ensures that every student’s progress is measurable, meaningful, and aligned with their individual potential.
-
Key focus areas include: Job readiness and career exploration Tutoring and Small Group Collaboration AfterSchool Programming/Arts And Crafts Academic improvement and educational success Financial management and decision-making skills Positive social interactions and leadership development Mental and emotional health awareness All Dream Big mentors and staff undergo extensive training and background checks to ensure the safety and well-being of every student. Each program year begins with a Kick-Off Celebration to welcome new participants and foster a sense of belonging and excitement for the journey ahead.
Before becoming an official 501(c)(3) nonprofit organization, Dream Big operated informally for more than seven years, serving over 500 boys and girls throughout Chicago’s South Side. Many of these students entered the program performing two to three grade levels behind, yet through the dedication of our volunteers and educators, we successfully developed individualized plans to help every student reach — and often exceed — grade-level proficiency.
Today, our structured mentoring model continues this legacy of excellence. Students meet with mentors and staff for approximately 20 hours per week over a 12-month period, engaging in activities centered around goal setting, academic support, and personal development. Mentors motivate students through positive reinforcement, recognition of achievements, and celebrations of progress.
Our Impact and Commitment
At Dream Big, we understand that true transformation begins with the entire family. That’s why our program offers family engagement sessions to strengthen relationships between parents, students, and schools. We provide guidance on how families can effectively support their children’s academic and personal development.
On a monthly or bi-monthly basis, we also invite professionals from our network of social workers and mental health experts to host presentations and activities for students and parents. These sessions not only offer valuable resources but also work to eliminate the stigma surrounding mental health support in our communities.
Dream Big believes in expanding horizons. Our monthly or bi-monthly field trips allow students to explore Chicago and experience opportunities beyond their immediate neighborhoods. From visits to colleges and museums to cultural and professional institutions, these outings serve as both educational enrichment and motivational incentives for continued growth.
To ensure the success of our initiatives, Dream Big uses evidence-based assessment tools, including the STEP Literacy Assessment, developed by the University of Chicago Urban Education Institute. Our structured evaluation process includes:
-
Assessing student needs and identifying goals
-
Conducting instructional and environmental analysis
-
Developing customized learning and mentoring strategies
-
Creating and revising instructional materials
-
Conducting formative and summative evaluations
This ongoing evaluation ensures that every student’s progress is measurable, meaningful, and aligned with their individual potential.
-
Key focus areas include: Job readiness and career exploration Tutoring and Small Group Collaboration AfterSchool Programming/Arts And Crafts Academic improvement and educational success Financial management and decision-making skills Positive social interactions and leadership development Mental and emotional health awareness All Dream Big mentors and staff undergo extensive training and background checks to ensure the safety and well-being of every student. Each program year begins with a Kick-Off Celebration to welcome new participants and foster a sense of belonging and excitement for the journey ahead.
Before becoming an official 501(c)(3) nonprofit organization, Dream Big operated informally for more than seven years, serving over 500 boys and girls throughout Chicago’s South Side. Many of these students entered the program performing two to three grade levels behind, yet through the dedication of our volunteers and educators, we successfully developed individualized plans to help every student reach — and often exceed — grade-level proficiency.
Today, our structured mentoring model continues this legacy of excellence. Students meet with mentors and staff for approximately 20 hours per week over a 12-month period, engaging in activities centered around goal setting, academic support, and personal development. Mentors motivate students through positive reinforcement, recognition of achievements, and celebrations of progress.
Our Impact and Commitment
At Dream Big, we understand that true transformation begins with the entire family. That’s why our program offers family engagement sessions to strengthen relationships between parents, students, and schools. We provide guidance on how families can effectively support their children’s academic and personal development.
On a monthly or bi-monthly basis, we also invite professionals from our network of social workers and mental health experts to host presentations and activities for students and parents. These sessions not only offer valuable resources but also work to eliminate the stigma surrounding mental health support in our communities.
Dream Big believes in expanding horizons. Our monthly or bi-monthly field trips allow students to explore Chicago and experience opportunities beyond their immediate neighborhoods. From visits to colleges and museums to cultural and professional institutions, these outings serve as both educational enrichment and motivational incentives for continued growth.
To ensure the success of our initiatives, Dream Big uses evidence-based assessment tools, including the STEP Literacy Assessment, developed by the University of Chicago Urban Education Institute. Our structured evaluation process includes:
-
Assessing student needs and identifying goals
-
Conducting instructional and environmental analysis
-
Developing customized learning and mentoring strategies
-
Creating and revising instructional materials
-
Conducting formative and summative evaluations
This ongoing evaluation ensures that every student’s progress is measurable, meaningful, and aligned with their individual potential.
-