High School Scholarships
Partial scholarships that supplement family contributions and a school's financial aid, opening the door to Chicago's leading private high schools.
Scholarships · Academic Support · College Access
Big futures begin with HighSight.
For Chicago students from low-income families, HighSight opens the door to a great high school — then walks alongside them with tutoring, mentoring, and college counseling all the way to a four-year degree.
For nearly 20 years, 100% of HighSight scholars have enrolled in college — each with a full-tuition scholarship.
Our mission
HighSight sees untapped potential others overlook — and provides the scholarships, academic support, and mentoring that help promising Chicago students excel in high school and graduate from four-year colleges across the country.
What we do
A four-year partnership, not a one-time gift
Every HighSight scholar receives wraparound support designed to carry them from eighth grade to a college degree.
Academic Support & Tutoring
Tutoring and academic coaching twice a week throughout the school year — building study habits, test prep, and organization alongside homework help.
College & Financial Aid Counseling
Personalized college counseling and financial-aid guidance for scholars and families. The result: 100% of our scholars enroll in college.
Leadership & Mentoring
Mentoring, leadership coaching, and personal-development workshops that help scholars grow into confident, capable young adults.
1,000+
Scholars graduated since 1992
20+
Partner private high schools in Chicago
100%
College enrollment for nearly 20 years
90%
Scholars consistently on the honor roll
Why it works
We take a chance on students others pass over
HighSight welcomes eighth-graders scoring below the 65th percentile and helps them become thriving high-school scholars. The transformation is real: 90% land consistently on the honor roll, and 100% earn full-tuition scholarships from the colleges they attend.
Twice-weekly tutoring, summer bridge programs, paid internships, and personalized college counseling combine into one powerful promise — that potential, given the right support, becomes achievement.
Save the date
HighSight Scholarship Gala
Join us in celebrating the Class of 2026. An evening of dinner, conversation, and inspiring scholar stories — with every dollar supporting the HighSight Scholarship & Program Fund.
- When
- Thursday, May 28, 2026
- 5:30 p.m. – 8:30 p.m.
- Where
- Wintrust's Grand Banking Hall
- 231 South La Salle Street, Chicago, IL
Make an impact
Help a Chicago scholar reach college
Whether you give, tutor, or share our story, you become part of a community that turns potential into possibility — one student at a time.