Principal Jobs in Chicago, IL
Principal jobs in Chicago are in strong demand, concentrated in the Loop, the Near North Side, and along the North Shore corridor, across education, management consulting, and professional services. Employers hiring right now include Northern Trust, Options Clearing Corporation, and TransUnion. Scan the live roles below and apply to whichever ones fit.
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Showing 5 of 103+ Principal jobs
JOB DESCRIPTION -
CLASS TITLE: Assistant Principal
CHARACTERISTICS OF THE CLASS: Under the direction of the school principal, takes charge of the school in the absence of the school principal, and assists in the direction and coordination of educational, administrative, supervisory, and counseling activities at school, and performs related duties as required.
ESSENTIAL FUNCTIONS: Under the direction of the principal, performs any of the following duties:
- Assists in the development and implementation of the School Improvement Plan for Advancing Academic Achievement (SIPAAA)
- Participates in the development and monitoring of the local school budget
- Plans and supervises student activity programs
- Provides individual and group guidance to students for personal problems, and educational and vocational objectives
- Takes or recommends disciplinary action for students or employees in violation of established discipline codes
- Meets with parents and guardians to review student progress or problems
- Supervises students at assemblies and social and athletic events
- Directs and coordinates teacher supervision of lunchrooms, corridors, and playgrounds
- Observes teachers' and career service personnel's performance and provides recommendations regarding performance to the school principal
- Assists principal in interviewing and recommending teacher and career service candidates for employment
- Assists in supervising student teachers assigned at the school
- Assists in making arrangements for and overseeing substitute teachers at the school
- Responds to inquiries and complaints from students, parents and guardians, local school council members, and the general public concerning school operating policies and procedures
OTHER FUNCTIONS: May teach courses, may organize and conduct in-service teacher and career service training at the school, may accompany students on field trips; may sponsor clubs, activities, and athletics.
MINIMUM QUALIFICATIONS:
Training and Experience: Must possess a Master's degree from an accredited college or university.
Certificate Requirement: Must possess a valid Type 75 Educational Administrative Certificate issued by the Illinois State Board of Education.
Knowledge, Abilities, and Skill:
- Thorough knowledge of the principles and practices of elementary and secondary education
- Thorough knowledge of the rules and regulations of the Chicago Public Schools
- Good knowledge of school budgeting methods and procedures
Ability to work with and for school-aged children, ability to establish and maintain effective working relationships with teachers and career service staff, parents and guardians, volunteers, local school council members, and community organizations.
Excellent interpersonal skills, good supervisory skills, excellent oral and written communication skills.
Physical Requirements: Light work: Exerting up to twenty (20) pounds of force occasionally, or up to ten (10) pounds of force frequently, or a negligible amount of force constantly to move objects. Physical demands include the ability to reach, handle, and finger objects; talk and hear; frequent use of near visual acuity and occasional use of far visual acuity.
Benefits:
Health & Wellness: Your Care, Your Choice
CPS is committed to providing comprehensive health coverage to our employees and their eligible dependents. You'll have access to a variety of choices to best fit your needs:
- Medical Plan Options
- Pharmacy
- Dental
- Vision
- Behavioral Health & EAP
- Employee Wellness Program
Financial Security: Planning for Today and Tomorrow
We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:
- Basic Life Insurance
- Life and Disability Insurance
- Pension Plans
- Supplemental Retirement Plans (403(b) and 457(b))
- Flexible Spending Accounts (FSAs)
- Spot Pet Insurance
Work-Life Balance: Supporting Your Personal and Professional Life
CPS values the well-being of its employees and offers competitive paid time off policies:
- Paid Leave
- Sick Leave
- Vacation Days
- Parental Leaves
- Short-Term Disability
- Religious Holidays
- Leaves
Reference the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.
Location: North/Northwest Side-1518 West Granville Avenue (Stephen K Hayt School)
Salary Range: $127,629.00 to $156,815.00
Posting Date: Oct 30, 2026, 4:05:19 PM
JOB DESCRIPTION -
CLASS TITLE: Assistant Principal
CHARACTERISTICS OF THE CLASS: Under the direction of the school principal, takes charge of the school in the absence of the school principal, and assists in the direction and coordination of educational, administrative, supervisory, and counseling activities at school, and performs related duties as required.
ESSENTIAL FUNCTIONS: Under the direction of the principal, performs any of the following duties:
- Assists in the development and implementation of the School Improvement Plan for Advancing Academic Achievement (SIPAAA)
- Participates in the development and monitoring of the local school budget
- Plans and supervises student activity programs
- Provides individual and group guidance to students for personal problems, and educational and vocational objectives
- Takes or recommends disciplinary action for students or employees in violation of established discipline codes
- Meets with parents and guardians to review student progress or problems
- Supervises students at assemblies and social and athletic events
- Directs and coordinates teacher supervision of lunchrooms, corridors, and playgrounds
- Observes teachers' and career service personnel's performance and provides recommendations regarding performance to the school principal
- Assists principal in interviewing and recommending teacher and career service candidates for employment
- Assists in supervising student teachers assigned at the school
- Assists in making arrangements for and overseeing substitute teachers at the school
- Responds to inquiries and complaints from students, parents and guardians, local school council members, and the general public concerning school operating policies and procedures
OTHER FUNCTIONS: May teach courses, may organize and conduct in-service teacher and career service training at the school, may accompany students on field trips; may sponsor clubs, activities, and athletics.
MINIMUM QUALIFICATIONS:
Training and Experience: Must possess a Master's degree from an accredited college or university.
Certificate Requirement: Must possess a valid Type 75 Educational Administrative Certificate issued by the Illinois State Board of Education.
Knowledge, Abilities, and Skill:
- Thorough knowledge of the principles and practices of elementary and secondary education
- Thorough knowledge of the rules and regulations of the Chicago Public Schools
- Good knowledge of school budgeting methods and procedures
Ability to work with and for school-aged children, ability to establish and maintain effective working relationships with teachers and career service staff, parents and guardians, volunteers, local school council members, and community organizations.
Excellent interpersonal skills, good supervisory skills, excellent oral and written communication skills.
Physical Requirements: Light work: Exerting up to twenty (20) pounds of force occasionally, or up to ten (10) pounds of force frequently, or a negligible amount of force constantly to move objects. Physical demands include the ability to reach, handle, and finger objects; talk and hear; frequent use of near visual acuity and occasional use of far visual acuity.
Benefits:
Health & Wellness: Your Care, Your Choice
CPS is committed to providing comprehensive health coverage to our employees and their eligible dependents. You'll have access to a variety of choices to best fit your needs:
- Medical Plan Options
- Pharmacy
- Dental
- Vision
- Behavioral Health & EAP
- Employee Wellness Program
Financial Security: Planning for Today and Tomorrow
We understand the importance of financial stability, which is why CPS offers strong retirement and savings options:
- Basic Life Insurance
- Life and Disability Insurance
- Pension Plans
- Supplemental Retirement Plans (403(b) and 457(b))
- Flexible Spending Accounts (FSAs)
- Spot Pet Insurance
Work-Life Balance: Supporting Your Personal and Professional Life
CPS values the well-being of its employees and offers competitive paid time off policies:
- Paid Leave
- Sick Leave
- Vacation Days
- Parental Leaves
- Short-Term Disability
- Religious Holidays
- Leaves
Reference the Chicago Public Schools: A Comprehensive Benefits Overview or the benefits handbook for comprehensive details.
Location: North/Northwest Side-1518 West Granville Avenue (Stephen K Hayt School)
Salary Range: $127,629.00 to $156,815.00
Posting Date: Oct 30, 2026, 4:05:19 PM
See All 103+ Principal Jobs in Chicago
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Find Principal JobsPrincipal Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Education
Principal Jobs in Chicago: Frequently Asked Questions
How do I get a principal job in Chicago?
Focus your search on Chicago's Loop-based consulting firms, the city's large public and charter school networks, and the professional services firms anchored in River North and Streeterville. Candidates who stand out typically combine demonstrated leadership in their discipline with deep familiarity with Chicago's specific institutional landscape, whether that means district-level education policy, financial services regulation, or management consulting at the city's major downtown firms.
Which companies hire principals in Chicago?
Employers hiring principals in Chicago right now include Northern Trust, Options Clearing Corporation, and TransUnion, based on current listings on Migrate Mate as of November 2026. Chicago's hiring mix skews toward large management consulting practices, urban public and charter school systems, and professional services firms with significant downtown footprints.
Are there remote principal jobs in Chicago?
Yes, though it depends heavily on the type of principal role: consulting and analytics-focused positions are far more remote-friendly than school-based or site-leadership roles, which are almost always on-site by nature. About 97% of principal openings tied to Chicago are remote or hybrid as of November 2026, with the flexibility concentrated in strategy, finance, and technology-adjacent tracks rather than education administration.
How can I get a principal job in Chicago with little or no experience?
The most realistic entry path in Chicago is lateral movement from a senior individual contributor or team lead role inside one of the city's large consulting, financial services, or education organizations. Chicago Public Schools and several major charter networks run leadership pipeline programs that promote internally, while downtown consulting firms often title strong senior associates as principals on a project basis. Building a record of cross-functional ownership within a Chicago institution is the clearest local on-ramp.
Which industries hire the most principals in Chicago?
Most principal openings in Chicago sit in Education, per current listings on Migrate Mate as of November 2026. Chicago's role as a hub for management consulting, financial services, and one of the country's largest public school systems means steady, year-round demand for principal-level leadership across all three sectors.
See All 103+ Principal Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
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