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Freelance Home Insurance Inspector Jobs in Chicago, IL

Orkin

Home Sales Inspector

Plainfield, IL · On-site

Responsibilities What You'll Be Doing · Conducting full-home inspections (from attic to crawl ... Insurance o 401(k) with company match o Paid vacation, sick leave, and holidays o Employee Stock ...

Orkin LLC

Home Sales Inspector

Plainfield, IL · On-site

$70K - $100K/yr

Responsibilities What You'll Be Doing • Conducting full-home inspections (from attic to crawl ... Insurance o 401(k) with company match o Paid vacation, sick leave, and holidays o Employee Stock ...

Orkin

Home Sales Inspector

Mokena, IL

Responsibilities What You'll Be Doing · Conducting full-home inspections (from attic to crawl ... Insurance o 401(k) with company match o Paid vacation, sick leave, and holidays o Employee Stock ...

Orkin LLC

Home Sales Inspector

Plainfield, IL · On-site

$70K - $100K/yr

Responsibilities What You'll Be Doing • Conducting full-home inspections (from attic to crawl ... Insurance o 401(k) with company match o Paid vacation, sick leave, and holidays o Employee Stock ...

Publicis Groupe Holdings B.V

Copy Editor

Chicago, IL · Hybrid

$53K - $79K/yr

... our freelancers and temporary employees. Voluntary benefit options include supplemental medical insurance, transportation, and parking benefits, legal benefits, pet insurance, and auto and home ...

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All JobsHome Insurance Inspector JobsFreelance Home Insurance Inspector JobsFreelance Home Insurance Inspector Jobs in Chicago, IL

Freelance Home Insurance Inspector information

See Chicago, IL salary details

$30.4K

$62.2K

$92.2K

How much do freelance home insurance inspector jobs pay per year?

As of Aug 25, 2026, the average yearly pay for freelance home insurance inspector in Chicago, IL is $62,165.00, according to ZipRecruiter salary data. Most workers in this role earn between $49,400.00 and $72,600.00 per year, depending on experience, location, and employer.

What is the difference between Freelance Home Insurance Inspector vs Home Appraiser?

AspectFreelance Home Insurance InspectorHome Appraiser
CredentialsInsurance-related certifications, sometimes state licensingReal estate or appraisal certifications, licenses
Work EnvironmentOn-site inspections of homes for insurance purposesProperty evaluations for market value
Employer & IndustryInsurance companies, brokers, or as independent contractorsReal estate firms, banks, appraisal companies
Search & Comparison IntentAssessing insurance risk, policy underwritingDetermining property value for sales or refinancing

While both roles involve property assessment, Freelance Home Insurance Inspectors focus on evaluating homes for insurance risk, requiring insurance-specific certifications. Home Appraisers determine property value for sales or refinancing, often with real estate certifications. The work environments and industry usage differ, but both require on-site inspections and industry-specific credentials.

Can you be a freelance home insurance inspector?

A freelance home insurance inspector is an independent professional who assesses properties for insurance purposes. They typically need knowledge of building codes, inspection skills, and may require relevant certifications or licenses, depending on the region. Freelance inspectors often set their own schedules and work on a contract basis for insurance companies or clients.

How do I become a freelance home insurance inspector?

To become a freelance home insurance inspector, you typically need a background in property assessment, construction, or related fields, along with knowledge of insurance requirements. Gaining relevant certifications, such as a home inspection license or appraisal training, can improve credibility. Building a network with insurance companies or adjusting firms and developing strong inspection skills are essential for success in this freelance role.

Is a freelance home insurance inspector a good side hustle?

A freelance home insurance inspector can be a viable side hustle for individuals with attention to detail and basic inspection skills. It often involves evaluating properties, completing reports, and may require certification or training. The flexibility allows for working around other commitments, but income can vary based on workload and experience.

Is there a big demand for freelance home insurance inspectors?

Demand for freelance home insurance inspectors is steady, as insurance companies and adjusting firms seek qualified professionals to assess property conditions for claims and underwriting. The role often requires knowledge of building standards, inspection skills, and sometimes certification, with opportunities increasing in regions experiencing higher property turnover or disaster recovery efforts.

What are the most commonly searched types of Home Insurance Inspector jobs in Chicago, IL?

The most popular types of Home Insurance Inspector jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Freelance Home Insurance Inspector jobs?

Cities near Chicago, IL with the most Freelance Home Insurance Inspector job openings:

Freelance Home Insurance Inspector jobs near you

Home Inspector

Crown Point, IN

Pillar To Post: The Tim James Team (Northwest Indiana)
See more jobs at Pillar To Post: The Tim James Team (Northwest Indiana)external

Full-time

Re-posted 6 days ago

Job description

Would you make a great home inspector? Let's talk!

Pillar To Post ® is the leading home inspection company in North America and locally our franchise has become the largest home inspection company in Northwest Indiana. Our goal is to make the home inspection experience educational and easy for our customers. Our team of inspectors use the latest innovation and technology to create customized home inspection reports and deliver them on site. Our talented team accomplishes the home inspection process with quality, integrity and exceptional customer service.

Locally, we own a franchise for Pillar To Post that services Lake, Porter, LaPorte, Jasper, and Newton Counties in Northwest Indiana. Our award-winning business is growing and we are looking to add to our team by offering an exciting opportunity for an aggressive self-starter who possesses dedication, professionalism and true people skills. This is a fast paced business with a reputation for quality, custom reports and outstanding customer service. We will train the right individual. Experience and qualifications will determine starting base pay.

Job Requirements:

  • Business minded
  • Strong attention to detail
  • Understand the importance of quality and consistent customer service
  • Basic knowledge of residential home systems and components
  • Ability to participate in local marketing events or programs
  • Excellent written and verbal communication skills
  • Great listening skills
  • Proficient computer skills
  • Have the aptitude and mental ability to problem solve and conduct professional conversations with real estate agents and customers
  • A great attitude, good presence and energy
  • Integrity and strong work ethic
  • Punctual and ability to work unsupervised
  • Reliable transportation with a valid driver’s license and insurance
  • Must be able to work in various weather conditions, climb ladders, walk on roofs, access crawl space, enter attics as well as stand for long periods of time
  • Ability to pass all employment screening and technical knowledge exam
  • Required to authorize background and driving checks
  • Available to work some evenings and weekends

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