8th Grade | High School Choice Teacher

Chicago, IL - Part Time

Job Summary
High Jump is hiring a High School Choice Teacher to join our Saturday Sessions for the 2026–2027 academic year.

The High School Choice (HSC) program helps middle school scholars better understand and navigate the high school process in Chicago. Throughout this process, scholars have opportunities to learn more about themselves, their identities, and what they want in high school and beyond.

The High School Choice Teacher will lead engaging, student-centered lessons and activities that help scholars explore high school options, understand the Chicago high school admissions process, and develop the skills and confidence to make informed decisions about their future. Teachers will facilitate a provided HSC unit plan and support scholars as they explore their interests, goals, and high school options.

Location

We are currently hiring a High School Choice Teacher at:

  • Francis W. Parker School (330 W Webster Ave, Chicago, IL 60614)

Teachers will work in person at one of these campuses for the Saturday Sessions.

We’re Looking For

  • Familiarity with the Chicago High School Application and admissions process and the range of options available to students.
  • Current or former CPS School Counselors or professionals with similar school-based counseling experience.
  • Comfortable facilitating a classroom using a provided unit plan and adapting instruction to student needs.
  • Able to build strong relationships with middle school students and help them feel confident navigating their high school options.

What You’ll Do

  • Facilitate the provided High School Choice criculum and lead engaging, student-centered lessons.
  • Help scholars understand Chicago high school options, pathways, application requirements, and timelines.
  • Guide scholars in identifying their interests, goals, and priorities when considering high school options.
  • Support scholars in researching, comparing, and evaluating schools.
  • Prepare scholars for high school fairs, school visits, and other high school exploration opportunities.
  • Create a welcoming classroom environment where scholars feel comfortable asking questions and advocating for themselves.
  • Communicate with Teaching Assistants and High Jump staff about student needs and progress.
  • Adjust lessons and activities to support different student needs.

Schedule & Dates
Time: 7:45 AM–2:30 PM
Saturday Program Dates:

  • September 26
  • October 3, 17 (High School Fair), 24
  • November 14 (ISEE Testing)
  • December 5, 12
  • January 9, 23
  • February 20
  • March 6
  • April 3, 10, 24
  • May 1, 15 (Tentative Make-Up Session)

Professional Development
All Saturday program staff will participate in one day of professional development. Please tentatively hold September 19, 2026.

Qualifications

  • Must be at least 18 years of age.
  • Associate's degree required; bachelor's degree preferred.
  • Experience working with middle school students or in organizations that serve youth.
  • Experience teaching, facilitating, or leading activities in an educational or youth-serving setting.
  • Strong communication and classroom management skills.
  • Ability to develop and facilitate an engaging course for middle school students.
  • Commitment to creating a positive and inclusive learning environment.

Pay
The pay range for teachers varies based on experience and certification, typically ranging from $28–$40 per hour.

References
Please provide two professional references as part of your application.

Other Saturday Teaching Opportunities
High Jump is also hiring Saturday Teachers for other subject areas and campuses. Explore our other Math, Science, Elective and High School Choice opportunities.

View all open High Jump positions here.
View all class descriptions here. 

Apply: 8th Grade | High School Choice Teacher
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