Chicago Principals & Administrators Association

New Voluntary Supplemental Benefits

Guaranteed Acceptance

No Medical Questions, Exams or Blood Tests.*

ICE Crisis Response

Protect yourself and your students.
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Member Benefits

From professional development resources to discounts on vacations, 
there's lots of reasons to become a member!

Breaking News

APs ARE Foundational

If you need help balancing the books, ask the leaders who manage their own abysmal budgets every year; we continuously find solutions that aren’t this detrimental to our children.

URGENT Member Update -- May 12, 2026

This morning, CPAA participated in the District’s budget briefing with other labor partners. We were disappointed to learn that approximately 120 assistant principal positions have been removed from foundational staffing in the upcoming budget.

Five Outstanding Students Earn AFSA’s 2026 Diann Woodard Scholarship

Five exceptional students are beginning their college journeys with support from the American Federation of School Administrators (AFSA), which has awarded them the 2026 Diann Woodard S

Long Term Care, Dental, Accidental Death and Dismemberment

AFSA Members are automatically eligible to participate in optional Long Term Care, Dental, Accidental Death and Dismemberment Insurance Benefits. 

Not Available in Puerto Rico or US Virgin Islands.

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Maximize Your AFSA Benefits for 2026

Your monthly investment in AFSA provides a number of benefits including a host of insurance policies. However, AFSA must have your most current information on file, or you will not qualify for these benefits or you may be denied coverage.

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Featured Benefits

Professional Development (Illinois Administrators' Academy)

Every school leader must complete an Illinois Administrators’ Academy course once a year to keep his or her license c

AFSA Professional Liability Insurance

AFSA provides protection for working members in good standing in case of an unfavorable judgment in a lawsuit naming members as parties or defendants.

AFSA Legal Action Trust

AFSA provides up to $25,000 of coverage for defense costs associated with denial of constitutional rights, “failure to educate” and criminal charges arising from school activities, when regular members in good standing are named as parties or defendants, provided that there is complete exoneration of the criminal charges.

Vacation on Land or by Sea

AFSA Travel, developed in partnership with Council of School Supervisors and Administrators (CSA), Local 1 is excited to resume offering travel programs around the world.
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Recent News

Mother’s Day Isn’t Easy for Every Student — Schools Can Do Better

Some students have lost their mother, while others live apart from her due to divorce, incarceration, military deployment, or other complex circumstances.

Advocacy in Action

We are in budget season… and although CPS has not released next year’s budget yet, we are already bracing for what will be missing. ( $1B State deficit; Federal fund revoked) Federal funding helped carry schools through COVID. It helped us rebuild. In some areas, we are finally seeing gains again. And now that funding is going away. So what does that mean for the progress we’ve made? Especially when we know that the needs in our schools haven’t decreased… they’ve increased.

Clarence Allen: From Newark Student to Newark School Leader

“As a principal, you’re everything to everyone,” Clarence says. “Our children are our most precious jewels. We have to treasure them. Students need leaders who are passionate about their growth and who hold themselves and other educators accountable.”

NAESP Names New Executive Director

The National Association of Elementary School Principals (NAESP) announced that its Board of Directors has selected Stephanie A. Morris as the organization’s next executive director. Morris will assume the role on August 1, 2026, following a planned leadership transition.

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