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

AP's Are Essential and the Fight Continues

As we continue to confront the devastating realities of the proposed SY26-27 school budgets, I want to remind every member that CPAA’s first and most urgent priority has been fighting to protect Assistant Principals as foundational positions in every school.

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Take Action -- Hold Our Elected Board Members Accountable

TAKE ACTION! Contact your elected school board members (listed by district in the table below) and remind them that YOUR CHILDREN and THEIR SCHOOLS MATTER.

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.

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

The End of a School Year, The Enduring Work of Leadership

As another school year comes to an end, many of us find ourselves in a familiar place, looking back on the months behind us while already beginning to think about the year ahead. After years in education, first as a teacher, then assistant principal, and principal, I still find this season to be one of the most meaningful times of the year.

Voters Demand AI Guardrails and Trust Labor to Lead

New polling released by the AFL-CIO and Data for Progress shows an overwhelming, bipartisan demand for clear, enforceable guardrails to ensure that technology serves as a partner to progress rather than a risk to workers' rights.

New Book Highlights Critical Role of School Counselors in Today’s Schools

A new book by AFSA member, Dr. Wladimir Lewis-Thomas, offers timely insight into why school counseling remains one of the most essential pillars of student success.

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.
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