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Entry Level Contractor Jobs in Chicago, IL (NOW HIRING)

Four Seasons Hvac Inc

Entry Level Technician

Hobart, IN

$40K - $75K/yr

Entry-Level HVAC Technician Paid Training • Clear Career Path • Hands-On Experience • Take ... HVAC contractor in North America - is hiring motivated individuals ready to start at the ground ...

FOUR SEASONS MASTER

Entry Level Technician

Hobart, IN

$40K - $75K/yr

Entry-Level HVAC Technician Paid Training • Clear Career Path • Hands-On Experience • Take ... HVAC contractor in North America -- is hiring motivated individuals ready to start at the ground ...

Four Seasons Heating

Entry Level Technician

Hobart, IN · On-site

$40K - $75K/yr

Entry-Level HVAC Technician Paid Training • Clear Career Path • Hands-On Experience • Take ... HVAC contractor in North America - is hiring motivated individuals ready to start at the ground ...

Four Seasons Heating

Entry Level Technician

Chicago, IL · On-site

$40K - $75K/yr

Entry-Level HVAC Technician Paid Training • Clear Career Path • Hands-On Experience • Take ... HVAC contractor in North America - is hiring motivated individuals ready to start at the ground ...

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All JobsEntry Level Contractor JobsEntry Level Contractor Jobs in Chicago, IL

Entry Level Contractor information

See Chicago, IL salary details

$25.8K

$49.3K

$70.6K

How much do entry level contractor jobs pay per year?

As of May 28, 2026, the average yearly pay for entry level contractor in Chicago, IL is $49,273.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,700.00 and $53,600.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Entry Level Contractor, and why are they important?

To thrive as an Entry Level Contractor, you need a basic understanding of construction principles, safety practices, and often a high school diploma or equivalent. Familiarity with hand and power tools, safety certifications like OSHA 10, and the ability to read blueprints are typically required. Strong work ethic, communication skills, and a willingness to learn help you stand out in this role. These skills and qualities are important because they ensure safe, efficient, and high-quality work on construction sites while supporting team collaboration.

What types of projects and responsibilities can an entry level contractor expect to handle in their first year?

As an entry level contractor, you can expect to work on a variety of foundational tasks such as assisting with project documentation, performing site visits, helping to ensure compliance with safety regulations, and supporting more experienced team members with daily operations. You may also be responsible for communicating with suppliers, tracking project progress, and learning industry-specific software. These tasks are designed to provide hands-on experience, familiarize you with project workflows, and help build relationships with colleagues and clients, all of which are essential for growth in the contracting field.

What are entry level contractors?

Entry level contractors are individuals who are just starting their careers in a particular trade or industry and work on a contract basis, rather than as full-time employees. They typically perform tasks under supervision, gaining hands-on experience while learning industry standards and safety protocols. Entry level contractors may work in fields such as construction, IT, or engineering, and their responsibilities usually focus on supporting more experienced professionals, assisting with projects, and developing specialized skills. These positions often serve as a stepping stone to more advanced roles within the industry.

What is the difference between Entry Level Contractor vs Apprentice Carpenter?

AspectEntry Level ContractorApprentice Carpenter
Required CredentialsHigh school diploma, basic safety trainingTypically in training, may have basic safety courses
Work EnvironmentSupervised construction sites, project-basedOn-site learning under supervision, hands-on training
Employer & Industry UsageConstruction companies, general contractingCarpentry apprenticeships, union or non-union programs
Common Search & ComparisonYesYes

Entry Level Contractors and Apprentice Carpenters both start their careers in construction, but Entry Level Contractors often have more responsibilities and may handle project coordination, while Apprentice Carpenters focus on learning carpentry skills under supervision. Both roles require safety training and are common entry points into the construction industry.

What are the most commonly searched types of Contractor jobs in Chicago, IL? The most popular types of Contractor jobs in Chicago, IL are:
What are popular job titles related to Entry Level Contractor jobs in Chicago, IL? For Entry Level Contractor jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Entry Level Contractor jobs in Chicago, IL look for? The top searched job categories for Entry Level Contractor jobs in Chicago, IL are:
Entry Level Contractor jobs near you
Entry Level Technician

Entry Level Technician

Four Seasons Hvac Inc

Hobart, IN

$40K - $75K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 16 days ago

Job description

Entry-Level HVAC Technician
Paid Training • Clear Career Path • Hands-On Experience • Take-Home Truck
Location: Hobart
Pay Range: $40,000 - $75,000+ (base pay + commission opportunities)
Start Your HVAC Career with the Industry Leader
Four Seasons Heating, Air Conditioning, Plumbing & Electric - the largest residential HVAC contractor in North America - is hiring motivated individuals ready to start at the ground floor and build a long-term career.
No guesswork. No dead-end job.
We invest in you with paid training, real-world experience, and a clear path to advancement.
Why This Role Is a Great Career Move
  • Paid, hands-on training (ride-alongs + classroom + field work)
  • Year-round, steady work - no seasonal layoffs
  • Clear promotion path from Entry-Level to Full-Service Technician
  • Company vehicle you take home (less commuting, faster mornings)
  • Low on-call rotation - only 1 out of every 6 weeks
  • Earn more as you learn with commission opportunities
What You'll Be Doing
As an Entry-Level HVAC Technician, you'll work alongside experienced professionals while learning the trade the right way.
You will:
  • Perform clean-and-check inspections on residential & light commercial HVAC systems
  • Assist senior technicians on service calls
  • Learn basic repairs and diagnostics under supervision
  • Maintain tools, truck, and job sites professionally
  • Build the skills needed to advance into a full-service technician role
What We're Looking For
  • HVAC Trade School completion
  • EPA Certification (Type I, II, or Universal)
  • Valid driver's license with acceptable driving record
  • Willingness to work overtime, weekends, and holidays when needed
  • Strong communication skills
  • Dependable, motivated, and eager to learn
What We Offer You
Pay & Career Growth
  • Competitive hourly pay plus commission opportunities
  • Paid training and ongoing education
  • Advancement opportunities based on performance - not tenure
Work-Life Perks
  • Take-home service vehicle
  • Company uniforms and cell phone
  • Authorized time off
  • Predictable on-call schedule
Benefits
  • Medical Insurance (employer subsidized)
  • Accident Insurance
  • Critical Illness Insurance
  • Hospital Indemnity Insurance
  • Dental Plans (free to employees)
  • Vision Plans (free to employees)
  • Short Term Disability (free to employees)
  • Long Term Disability
  • Basic Life Insurance (free to employees)
  • Holiday Pay
  • Paid Time Off
  • 401k with Matching
  • Credit Union
  • Cellular Discounts
  • Tuition Reimbursement

Join a Company That Invests in You
At Four Seasons, we don't just train technicians - we build careers.
If you're ready to learn a valuable trade, earn strong pay, and grow with a company that promotes from within, we want to meet you.
Equal Opportunity Employer & Reasonable Accommodation
Four Seasons is an affirmative action and equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. Four Seasons is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities. To request reasonable accommodation, contact Human Resources at 773-284-6161 Ext 5010.

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