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2021 Principal Appreciation Campaign

October is national Principal Appreciation Month! 2021 marks the sixth year of Chicago’s citywide Principal Appreciation Campaign, when we join forces with school communities, city officials and corporate leaders to lift up the great work of our hardworking school leaders. In 2021, principals have continued to lead school communities through a global pandemic, making it possible for a return to five-day a week in-person learning. 

Chicago’s public school principals oversee more than 600 schools and impact over 350,000 students in the third-largest school district in the country. Thanking principals is one way that we can acknowledge their hard work and keep them in our schools.

2021 Principal Appreciation Events

PRINCIPAL HAPPY HOURS | Thursdays in October 2021

Looking for a time to decompress and connect with your principal peers? Looking for a fun and casual way to unwind after a long day? Or just looking for a good drink?

In October, The Fund is excited to host four happy hours for Chicago public school principals on Thursdays. Each week, the happy hour will rotate to a different part of the city. RSVP links can be found below:

Please keep in mind several notes:

  • *Special “Principal: Leading Us Forward” Storytelling Event: On October 21, there will be a special three-hour principal appreciation month happy hour, taking place in the Museum of Science and Industry’s Henry Crown Space Center. This event will end with a live storytelling event titled, “Principals: Leading Us Forward.” From 6:00-7:00PM, in the Giant Dome Theater, a group of principals will share their personal stories of strength and leadership. Any individuals unable to attend the event in-person will also be able to register for a virtual ticket to watch the event’s storytelling section.
  • COVID-19 Safety: We are implementing all possible measures to make sure that these events are COVID-19 safe. Masks will be required whenever not eating or drinking, and any non-CPS employee guests will be required to show proof of vaccination before entry. Among the four venues, two of them are have outdoor spaces, while the other two are large enough for social distancing indoors.
  • Invitations: Because of COVID-19 restrictions, we are capping attendance at each happy hour — so please sign up ASAP! That being said, we are allowing principals to invite one guest — feel free to come alone, or invite your AP, a teacher on your team, or your partner! Or, message your peers to make sure to come to the same happy hour!
  • Free Parking: All events will have free parking available. Further details will be sent out in event reminders; we highly encourage all attendees with guests to carpool.
  • Photography: We will have an event photographer at each venue, so come prepared to take some nice photos
  • Social Media: Share any photos that you take on Facebook, Instagram, or Twitter and tag #PrincipalPrideChi.

2021 Principal Appreciation Raffles

In honor of 2021 Principal Appreciation Month, The Fund is hosting a weekly raffle where one principal will be chosen to receive prizes every Friday in October. Individuals must 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 will 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.  

This year, 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.