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Head Start Program Director Jobs in Chicago, IL (NOW HIRING)

Casa Central

Early Head Start Teacher

Chicago, IL · On-site

$46K/yr

Implement the agency mission, philosophy, and core values to direct daily work and decision-making ... Program-Specific Activities Ensure compliance with all Early/Head Start Program Performance ...

START EARLY

Early Head Start Teacher

Waukegan, IL

  • Medical

  • Retirement

The Early Head Start Teacher works closely with the Lead Teacher to create comprehensive and ... Programs and Family Service Plans, providing tailored support for every child as directed by Lead ...

Start Early

Early Head Start Teacher

Waukegan, IL · On-site

  • Medical

  • Retirement

The Early Head Start Teacher works closely with the Lead Teacher to create comprehensive and ... Programs and Family Service Plans, providing tailored support for every child as directed by Lead ...

Start Early

Teacher Assistant, Head Start

Chicago, IL · On-site

$15.25 - $19.50/hr

  • Medical

  • Retirement

As a program that serves low-income families, Educare's research-based program helps children ... The Head Start Teacher Assistant works cooperatively with the Lead Teacher to plan and implement ...

START EARLY

Teacher Assistant, Head Start

Chicago, IL

$40K - $41K/yr

  • Medical

  • Retirement

As a program that serves low-income families, Educare's research-based program helps children ... The Head Start Teacher Assistant works cooperatively with the Lead Teacher to plan and implement ...

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All JobsHead Start Program JobsHead Start Program Director JobsHead Start Program Director Jobs in Chicago, IL

Head Start Program Director information

See Chicago, IL salary details

$30.4K

$80.6K

$141.2K

How much do head start program director jobs pay per year?

As of Aug 19, 2026, the average yearly pay for head start program director in Chicago, IL is $80,616.00, according to ZipRecruiter salary data. Most workers in this role earn between $54,600.00 and $95,400.00 per year, depending on experience, location, and employer.

What is a Head Start Program Director?

A Head Start Program Director is responsible for overseeing the operations of a Head Start program, which provides early childhood education, health, nutrition, and parent involvement services to low-income children and their families. The director manages staff, ensures compliance with federal and state regulations, develops program policies, and oversees budgets and grants. Their goal is to ensure that children are prepared for school and that families receive the support they need. This role also involves collaborating with community organizations and engaging with parents to strengthen program outcomes.

What are the key skills and qualifications needed to thrive as a Head Start Program Director?

To thrive as a Head Start Program Director, you need expertise in early childhood education, program administration, and regulatory compliance, typically supported by a bachelor's or master's degree in education or a related field. Familiarity with Head Start Performance Standards, ChildPlus software, and grant management systems is essential. Strong leadership, communication, and problem-solving skills help in managing staff, building community partnerships, and ensuring program quality. These competencies are crucial for delivering high-quality educational services to children and families while maintaining compliance with federal and state requirements.

What are some common challenges faced by Head Start Program Directors, and how can candidates prepare for them?

Head Start Program Directors often navigate challenges such as balancing compliance with federal regulations, managing diverse teams, and ensuring high-quality early childhood education for all children served. Candidates should be prepared to implement effective systems for staff supervision, budget management, and community engagement. Developing strong organizational, communication, and problem-solving skills is essential for addressing these challenges and fostering a positive, supportive environment for both staff and families.

What is the difference between Head Start Program Director vs Head Start Center Supervisor?

AspectHead Start Program DirectorHead Start Center Supervisor
CredentialsBachelor's degree in early childhood education or related field; experience in program managementHigh school diploma or associate's degree; experience in early childhood education or supervision
Work EnvironmentOversees multiple centers or programs, administrative settingManages daily operations of a single center, direct supervision of staff
ResponsibilitiesProgram planning, compliance, staff management, community relationsStaff supervision, classroom quality, parent engagement, daily operations

The Head Start Program Director typically oversees multiple centers and handles administrative and strategic responsibilities, requiring higher credentials. In contrast, the Head Start Center Supervisor manages daily operations at a single center, focusing on staff and classroom quality. Both roles are vital but differ in scope and level of responsibility.

What are popular job titles related to Head Start Program Director jobs in Chicago, IL?

For Head Start Program Director jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Head Start Program Director jobs in Chicago, IL look for?

The top searched job categories for Head Start Program Director jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Head Start Program Director jobs?

Cities near Chicago, IL with the most Head Start Program Director job openings:

Head Start Program Director jobs near you
Infographic showing various Head Start Program Director job openings in Chicago, IL as of August 2026, with employment types broken down into 80% Full Time, 15% Part Time, and 5% Contract. Highlights an 95% In-person, and 5% Remote job distribution, with an average salary of $80,616 per year, or $38.8 per hour.

Head Start Teacher Assistant

NORTHWESTERN SETTLEMENT

Chicago, IL • On-site

Full-time

Re-posted 22 days ago

Job description

Job Title:          Head Start Teacher AssistantReports to:       Director of Early Childhood EducationCompensation: $43,0000 to $45,000 Annually + Robust Benefits Package Status:               Full timeLocation:           Chicago, IL

For over a century, Northwestern Settlement has been a cornerstone in the West Town community, supporting families through education, social services, and the arts. Our Early Childhood Program is a vital part of that mission, fostering a safe, nurturing, and educational environment for young children during their most critical years of development. We are currently seeking a dedicated and passionate Head Start Teacher Assistant to join our team. This individual will support the Lead Teacher in planning and implementing developmentally appropriate activities that support the physical, cognitive, emotional, and social development of children. The Head Start Teacher Assistant works collaboratively to assist with the development and implementation of core curriculum that follows the Head Start Program Performance Standards, NAEYC Standards, and that of our Community Partnership CPS. This opportunity is ideal for someone who has a passion for helping young children grow and thrive.

Key Duties/Responsibilities

  • Assist with creating a inclusive and supportive classroom environment

  • Support implementation of lesson plans aligned with Creative Curriculum System for Preschool

  • Help monitor and document children’s progress through observations and assessments

  • Participate in  parent-teacher conferences to support individualized child development plans

  • Foster open communication with families and promote parent involvement

  • Maintain a safe and clean learning environment in compliance with DCFS and Head Start regulations

  • Participate in ongoing professional development, team meetings, and trainings

  • In addition to the duties expressly provided above, the Head Start Teacher Assistant from time to time will perform other duties and functions as assigned by their direct supervisor.

Ideal Skills/Traits

  • Bilingual in English/Spanish preferred

  • Excellent oral and written communication, collaboration, and organizational skills 

  • Ability to relate to our multicultural community

  • Ability to accept guidance and supervision

  • Excellent punctuality and attendance

  • Skilled in data entry and database management

Education/Experience

  • Associate Degree in Early Childhood Development, or related field that includes 15
    semester hours in Early Childhood Education

  • Illinois Gateways ECE/ IT Credential Level 4

  • American Red Cross First Aid/CPR Certification

  • Complete all forms upon offer and acceptance as per DCFS, City of Chicago and Head Start
    licensing standards (including 3 letters of recommendation, Criminal Background Check,
    Fingerprinting and Childs Abuse and Neglect Background Check, etc…)

Compensation & Benefits:

Compensation will be commensurate with experience and qualifications. We offer a robust health benefits package. In addition, all staff members are equipped with the tools needed to succeed, including a dedicated workspace, laptop, email, high-speed internet access, and all necessary supplies.

Statement of Non-Discrimination:

Northwestern Settlement is proud to be an equal opportunity employer, making all employment decisions, including recruiting, hiring, training, and promoting without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status or any other characteristic or classification protected by law.

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