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Head Guide Jobs in Chicago, IL (NOW HIRING)

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Early Head Start Teacher

Waukegan, IL

... learners guides everything we do. As a leader in early learning and care, we scale our deep ... The Early Head Start Teacher works closely with the Lead Teacher to create comprehensive and ...

Start Early

Early Head Start Teacher

Waukegan, IL · On-site

... learners guides everything we do. As a leader in early learning and care, we scale our deep ... The Early Head Start Teacher works closely with the Lead Teacher to create comprehensive and ...

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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 2, 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.

Head Custodian

Naperville Community Unit School District 203

Naperville, IL • On-site

$18.95/hr

Full-time

Medical, Dental

Posted 22 days ago

Job description

Position Type:
Support Staff - Buildings & Grounds/Custodian/ Custodian - Full Time
Date Posted:
8/14/2026
Location:
3 - Connections (Transition Program)
# work weeks / year
52
# hours / day
8
Shift
Head Custodian
Hourly rate
$18.95
Annual shift stipend
$2.61
This position is governed by a collective bargaining benefits and eligible for health/dental insurance benefits.
**Internal NUMA applicants that apply within 5 days of the posted date will be guaranteed an interview**
Attachment(s):
  • 2026 Benefits Guide.pdf
  • Head Custodian - Elementary Job Description 2024.pdf

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