Chicago Principals & Administrators Association

New Voluntary Supplemental Benefits

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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

A Message from CPAA about May 1st Day of Civic Action

Today, along with many of our members, CPAA learned that CPS is considering amending the school calendar by designating May 1, 2026, as a Day of Civic Action with no student attendance.

School Leaders Bring Student Concerns to Capitol Hill

School leaders from across the country gathered on Capitol Hill last week, bringing urgent concerns about student mental health, school safety, and educator support directly to federal lawmakers. A

Oklahoma School Shooting Underscores Urgent Need to Protect School Leaders

Statement from American Federation of School Administrators (AFSA) President Mark Cannizzaro

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

CPAA In-Person Meeting for Assistant Principals

Assistant Principals:

We are calling an in-person meeting for assistant principals to get aligned on contract/bargaining priorities and strategy.

The reality is … APs are being asked to carry more, with fewer protections and without compensation that reflects the role. That includes everything from sick-day limitations to the added responsibilities many of you are taking on daily without adequate pay.

We are currently pushing on:

  • Longevity pay

  • AP salary structure

  • Guaranteed AP positions in every school

White House Releases FY27 Budget: Key Education Provisions and Proposed Changes

In the first week of April, the White House released its proposed FY27 budget, outlining top line goals, selected program increases, and proposed eliminations. The proposal marks the beginning of the FY27 appropriations process, which will move to Congress following the April recess.

KellyAnn DeSantis: An Assistant Principal Leading with a Passion for Language

“At the core of everything, we have to ground ourselves in the understanding that we’re working with children — and that leading with empathy must always come first.”

NAESP Recognizes 29 Assistant Principals as National Outstanding AP's

Twenty-nine school leaders from across the nation have been recognized by the National Association of Elementary School Principals as part of the 2026 class of National Outstanding Assistant Principals, highlighting the critical role assistant principals play in supporting students, staff, and school communities.

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