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2021 Principal Appreciation Campaign

2021 marked the sixth year of Chicago’s citywide Principal Appreciation Campaign, when we joined forces with school communities, city officials, and corporate leaders to lift up the great work of our hardworking school leaders. In 2021, principals continued to lead over 600 school communities with over 350,000 students through a global pandemic, making it possible for a return to five-day a week in-person learning. 

See the impact of the 2021 principal appreciation campaign here:

PAW Report_Final (1)

2021 Principal Appreciation Events

PRINCIPAL HAPPY HOURS | Thursdays in October 2021

In October, The Fund hosted four happy hours for Chicago public school principals on Thursdays. Each week, the happy hour rotated to a different part of the city. Event pages can be found below:


  • COVID-19 Safety: We implemented all possible measures to make sure that these events are COVID-19 safe. Masks were required whenever not eating or drinking, and all guests were required to show proof of vaccination before entry. Among the four venues, two of them had outdoor spaces, while the other two were large enough for social distancing indoors.
  • Invitations: Because of COVID-19 restrictions, we capped attendance at each happy hour.
  • Free Parking: All events had have free parking available.
  • Photos: See all photos from events here.


2021 Principal Appreciation Raffles

In honor of 2021 Principal Appreciation Month, The Fund hosted a weekly raffle where one principal was chosen to receive prizes every Friday in October. Individuals were required to be current Chicago public school principals in order to participate OR individuals can nominate their principals for a raffle prize. 
Fill out the following form in order to receive a chance to win! All participants in Fund events during October will automatically be entered. Weekly prizes include:
—October 8: $50 Visa Gift Card, Gift Vouchers to Flowers for Dreams, and Tickets to Shedd Aquarium
—October 15: $50 Visa Gift Card, Tickets to Shedd Aquarium, and Shedd Aquarium apparel
—October 22: $50 Visa Gift Card, Tickets to Shedd Aquarium, and Items from Lou Malnati’s Pizza
—October 29: $50 Visa Gift Card, Tickets to Shedd Aquarium, and a Gift Card to Brown Sugar Bakery

Winners were be announced on social media every Friday, and be notified via email and phone.

Principal Mental Health Resources

Throughout the pandemic, principals have emphasized the importance of social-emotional well-being for students and teachers — but too often, principals forget to take care of themselves, too. One mental health resource that can help educators is Headspace, an app designed to make room to create room for mindfulness and meditation, while combatting anxiety and stress.  

All educators can redeem free annual Headspace subscriptions here.

You must be 18 years of age, or the age of majority in your province, territory or country, to sign up as a registered user of the Products.

  • If you are new to Headspace, please click “create a new account.”
  • If you have an existing Headspace account, please click “I have an existing account” to enter your existing Headspace credentials.
  • After signing up or logging in, you will need to verify your school/district email address by entering your school email address (e.g.
  • You will then receive a confirmation email to that school email as a final step to redeem your free Headspace subscription.
  • Please reach out to for any troubleshooting.

Thank you to our 2021 sponsors and partners:



  • Illinois Principals Association
  • The Museum of Science and Industry
  • Shedd Aquarium
  • Blackhawks Foundation
  • Illinois Network of Charter Schools
  • Teach For America, Chicago NW Indiana
  • Latino Policy Forum
  • Fulcrum Education Solutions
  • Educators for Excellence
  • Teach Plus
  • Umoja
  • Lou Malanti’s Pizza
  • Flowers for Dreams
  • Brown Sugar Bakery

Invest in Chicago's Principals

Principals have an out-sized impact on their schools and communities. Any amount can make a difference.

Support Our Work

We aim to serve more than 600 principals and 360,000 students by 2023, with an emphasis on the schools that most need support.

Celebrate School Leaders

Every October, school communities, city officials, and corporate leaders join together to lift up the great work of principals.