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Head Guide Jobs in Chicago, IL (NOW HIRING)

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Early Head Start /PI Lead Teacher

Waukegan, IL · On-site

$14.25 - $19/hr

The Early Head Start/PI Lead Teacher works closely with the Education Coordinator to create ... Supervise and guide your EHS Teacher, fostering a collaborative atmosphere that enhances the ...

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All JobsHead Guide JobsHead Guide Jobs in Chicago, IL

Head Guide information

See Chicago, IL salary details

$143.7K

$164.8K

$183.4K

How much do head guide jobs pay per year?

As of Sep 3, 2026, the average yearly pay for head guide in Chicago, IL is $164,823.00, according to ZipRecruiter salary data. Most workers in this role earn between $154,500.00 and $175,100.00 per year, depending on experience, location, and employer.

What is a head guide?

Head Guides are experienced professionals who lead and oversee guiding teams, typically in outdoor adventure, tourism, or educational settings. They are responsible for ensuring the safety and satisfaction of clients, training and supervising other guides, and planning excursions or tours. Head Guides often act as the primary point of contact between guests and the organization, handling logistics, emergency situations, and customer feedback. Their leadership is crucial for creating memorable and safe experiences for clients. They may also help develop routes, maintain equipment, and ensure compliance with safety regulations.

What are the key skills and qualifications needed to thrive as a head guide?

To thrive as a Head Guide, you need expertise in outdoor leadership, risk assessment, and group management, typically supported by relevant certifications such as Wilderness First Responder or guiding licenses. Familiarity with GPS navigation tools, communication devices, and safety equipment is essential for this role. Outstanding interpersonal skills, decision-making abilities, and the capacity to remain calm under pressure help build trust and ensure group cohesion. These skills are vital for ensuring client safety, delivering exceptional experiences, and effectively handling emergencies in challenging environments.

What are some common challenges faced by a head guide and how can they be managed effectively?

As a Head Guide, one of the main challenges is balancing the safety and enjoyment of guests while managing a team of guides in dynamic outdoor environments. Unexpected weather, varying guest abilities, and logistical issues often require quick thinking and adaptability. Effective communication, strong leadership, and thorough planning are key to overcoming these obstacles. Building rapport with both guests and staff helps foster a positive experience and ensures smooth operations even when challenges arise.

What is the difference between Head Guide vs Tour Guide?

AspectHead GuideTour Guide
CredentialsOften requires experience, certifications in guiding or safetyTypically requires a guiding license or certification
Work EnvironmentLeads groups, manages guides, plans routesConducts tours, interacts directly with tourists
Employer & Industry UsageUsed in adventure, outdoor, and specialized tour companiesCommon across travel, city, and museum tours

The main difference is that a Head Guide oversees tour operations and manages guides, while a Tour Guide directly interacts with tourists, leading individual or group tours. The Head Guide has more responsibilities in planning and supervision, whereas the Tour Guide focuses on delivering the tour experience.

What are the most commonly searched types of Guide jobs in Chicago, IL?

The most popular types of Guide jobs in Chicago, IL are:

Head Guide jobs near you
Infographic showing various Head Guide job openings in Chicago, IL as of June 2026, with employment types broken down into 90% Full Time, 8% Part Time, 1% Temporary, and 1% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $164,823 per year, or $79.2 per hour.

Teacher Assistant Head Start 3-5

Mary Crane Center

Chicago, IL • On-site

$42K - $52K/yr

Full-time

Medical, Dental, Vision, PTO

Re-posted 7 days ago

Job description

Description:

Make a difference in a child’s future, every single day. Are you passionate about helping young children grow, learn, and thrive? Do you believe in the power of play, learning through experience, and strong family partnerships? If so, we’d love to welcome you to our team as a Teacher Assistant in our Early Childhood and Head Start programs. New hires are eligible for a $1,000 sign-on bonus (terms apply).


You’ll work side-by-side with a Lead Teacher to create joyful, developmentally rich classrooms where children feel safe, seen, and supported. This is more than a job, it’s a chance to shape lives, spark learning, and support families in your community.


What You'll Do

Support Learning & Play

  • Help implement engaging, age-appropriate activities using Creative Curriculum and Head Start standards
  • Supervise and interact with children during classroom time, meals, and play
  • Model respectful, positive behavior and guide children with gentle, consistent discipline
  • Promote family-style dining and healthy habits


Observe & Celebrate Growth

  • Assist with regular developmental assessments using tools like Creative Curriculum Checklists and Ages & Stages Questionnaires
  • Capture learning moments through observation notes, photos, and child portfolios


Collaborate with Families

  • Help coordinate and attend parent-teacher conferences and home visits
  • Communicate daily with parents about classroom routines, activities, and their child’s progress
  • Support families in engaging with the program and advocating for their child


Keep Our Classrooms Thriving

  • Assist with planning and preparing lesson materials
  • Help maintain a clean, safe, and organized learning space
  • Sanitize toys, surfaces, and equipment daily


Be a Team Player

  • Work closely with the Lead Teacher, Site Director, and other staff members
  • Mentor volunteers, teacher aides, and foster grandparents
  • Attend trainings, team meetings, and agency events as required


Requirements:

Education & Experience:

  • Associate’s Degree in Early Childhood Education or Child Development, OR 60 credit hours of which 15 hours are in early childhood
  • Gateways ECE Credential Level 4


Skills & Qualifications:

  • Strong communication skills (written and verbal); bilingual in Spanish preferred
  • Passion for early childhood development and family engagement
  • Collaborative, flexible, and open to feedback
  • Organized, detail-oriented, and committed to high-quality work
  • Ability to lift up to 30 lbs and work on the floor with children
  • Willingness to travel locally for home visits and meetings as needed


Why Join Us

  • Mission-driven work with real impact on children and families
  • Professional growth opportunities including CDA support, in-services, and workshops
  • Collaborative culture where your voice matters
  • Supportive leadership and experienced mentors


Compensation & Benefits
Mary Crane Center offers a comprehensive benefits package that includes access to medical, dental, and vision insurance (HMO, PPO, and DPPO options available), paid time off, and other employee wellness programs. Eligibility varies by position and hours worked. Additional benefit details will be provided during the hiring process.


Ready to inspire, nurture, and grow with us? Apply today and become part of a team that believes every child deserves a strong start.

We are an Equal Opportunity Employer and do not discriminate based on race, religion, color, sex, sexual orientation, gender identity, age, national origin, veteran status, or disability.


Reasonable accommodations will be provided as required by law. To request accommodations, please contact 773-242-2881 x2866.

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