Now accepting 5th–8th grade applications for 2026–27. See what middle school should feel like — schedule a visit.

The Middle School years are too important to waste.

Your child is becoming someone right now — forming opinions, testing boundaries, figuring out who they are. They need a school that matches that intensity with purpose. Bennett’s Middle School (5th–8th grade) pairs rigorous, cross-disciplinary projects with a community small enough to know every student by name — so your child is challenged, supported, and never invisible.

See It For Yourself

Cognia Accredited · 5th–8th Grade · Competency-Based Assessment · Advisory Program · 100% Graduation Rate · Chicago’s West Loop

Known and Supported

Every middle schooler has an advisor who knows them personally — their strengths, their struggles, their story. Your child won’t be a number in a grade book. They’ll be known.

Rigor That Fits the Age

Adolescents need intellectual challenge matched with emotional safety. Your child tackles 8–12-week cross-disciplinary projects, presents publicly, and builds competencies — not just compliance.

Growth You Can See

Competency-based assessment replaces vague letter grades with specific evidence of what your child can do, where they’re growing, and what’s next. You’ll know exactly where they stand.

Most Middle Schools Get These Years Wrong

The traditional middle school model asks adolescents to sit still and absorb content during the exact years their brains are wired to question, create, and connect. The result? Disengagement. Anxiety. Students who learn to perform for grades instead of learning to think. Your child deserves a school that was designed for how adolescents actually develop — not a high school model shrunk to fit a younger body.

See It For Yourself

See if Bennett Is Right for Your Middle Schooler

Tell us about your family. We'll reach out personally with information about visiting campus and scheduling a conversation with admissions.

What Rigor Really Looks Like

Three minutes inside a school where students don't just study subjects — they use them.

Built for How Adolescents Actually Learn

Assessment That Tells the Whole Story

Bennett’s competency-based model replaces the A-through-F guessing game with specific, evidence-backed feedback on your child’s strengths, growth areas, and next steps. Families see portfolios, narrative feedback, and the Mastery Transcript — not a single reductive number.

Advisory That Goes Deep

Every student is paired with an advisor who meets with them regularly, tracks their growth across all domains, and serves as the first call for families. Your child has one adult at school who sees the full picture — academic, social, emotional—and stays in their corner all year.

Assessment That Tells the Whole Story

Bennett’s competency-based model replaces the A-through-F guessing game with specific, evidence-backed feedback on your child’s strengths, growth areas, and next steps. Families see portfolios, narrative feedback, and the Mastery Transcript—not a single reductive number.

Social-Emotional Development, Embedded

Middle school is where identity forms. Bennett embeds self-awareness, relationship skills, and emotional regulation into daily life — not as an add-on program, but as a core part of what it means to be a student here. Your child builds confidence and character alongside academic skill.

A Clear Path to Upper School

Bennett is one school, PreK through 12th grade. Your middle schooler’s competencies, relationships, and record of learning carry forward seamlessly into an Upper School program that includes internships, advanced projects, and college preparation — with no disruption, no reapplication, and no starting over.

From Curiosity to Confidence — Every Year Builds on the Last.

Bennett Day School opened in 2014 with 23 students and a conviction that school should work the way the world actually works. Today, 410 students from preschool through 12th grade learn by doing in Chicago’s West Loop. Your middle schooler won’t just survive these years — they’ll be transformed by them.

See It For Yourself