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Freelance Home Insurance Inspector Jobs in Chicago, IL

Compliance Inspector

Joliet, IL ยท On-site

$20 - $22/hr

Medical/Dental/Vision insurance * Front loaded PTO * 401k - Company match up to 4% * Long and short ... With more than 50,000 homes under management, we're your all-in-one real estate solution.

Compliance Inspector

Joliet, IL ยท On-site

$20 - $22/hr

Medical/Dental/Vision insurance * Front loaded PTO * 401k - Company match up to 4% * Long and short ... With more than 50,000 homes under management, we're your all-in-one real estate solution.

Copy Editor

Chicago, IL ยท On-site

$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 ...

Vehicle Condition Inspector

Crystal Lake, IL

$16.50 - $21.25/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Chicago Heights, IL

$16.50 - $21.50/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Aurora, IL ยท On-site

$16.75 - $21.75/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Aurora, IL ยท On-site

$16.75 - $21.75/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Chicago Heights, IL ยท On-site

$16.50 - $21.50/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Chicago Heights, IL ยท On-site

$16.50 - $21.50/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Crystal Lake, IL

$16.50 - $21.25/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Crystal Lake, IL ยท On-site

$16.50 - $21.25/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Aurora, IL ยท On-site

$16.75 - $21.75/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Chicago Heights, IL ยท On-site

$16.50 - $21.50/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

Vehicle Condition Inspector

Aurora, IL ยท On-site

$16.75 - $21.75/hr

Travel to & from dealerships and homes to inspect, and write condition reports, list vehicles to ... Valid driver's license and use of a validly registered and insured motor vehicle required.

PLUMBING INSPECTOR

Westchester, IL ยท Hybrid

$6.7K - $9.5K/mo

... home. No matter what state career you're looking for, we offer jobs that fit your life and your ... Competitive Group Insurance benefits including health, life, dental and vision plans. * Pension ...

QA Inspector

Batavia, IL ยท On-site

$20 - $21/hr

... the home and industrial markets. A privately held company headquartered in Western Chicago ... Group Term Life insurance * 401K with employer match * Paid vacation time off * Paid holidays

Showing results 21-40

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 20, 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:

$20 - $22/hr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 11 days ago


Job description

Description

Westward360 is looking to add a Compliance Inspector to support our south suburb communities. This role is responsible for conducting routine compliance inspections of association common areas and, where permitted, individual lots or units. The Inspector plays a key role in helping communities maintain standards outlined in their Governing Documents while ensuring inspections are performed consistently, professionally, and objectively.


Westward360 is a leader in the Property Management industry, with locations across the map. We service condo, townhome, and homeowner associations, and provide rental management services to multi-family and single-unit properties.ย 


What we offer:

  • Compensation range of $20-$22 per hour
  • Mileage reimbursement
  • Medical/Dental/Vision insurance
  • Front loaded PTO
  • 401k - Company match up to 4%
  • Long and short term disability at no cost to employee


What you'll do:

Routine Compliance Inspections

  • Conduct scheduled compliance inspections at intervals determined by the Association
  • Inspect visible exterior areas of lots/units and accessible common elements without trespass
  • Observe conditions only from common areas, streets, sidewalks, or other lawful vantage points
  • Identify potential violations of Governing Documents, including but not limited to:
    • Landscaping maintenance
    • Exterior property condition and cleanliness
    • Architectural modifications or unapproved alterations
    • Parking violations
    • Trash, debris, and storage issues
    • Signage violations
    • Pet-related violations
    • Fence, wall, and gate conditions
    • Balconies, patios, and visible storage areas (where applicable)

Documentation and Reporting

  • Document all observed common area conditions using written descriptions and date-stamped photographs
  • Prepare inspection reports that include:
    • Area inspected
    • Description of observed conditions
    • Photographic evidence
    • Date and time of inspection
  • Submit inspection reports to the Association or Managing Agent within 24-48 hours, unless otherwise agreed
  • Utilize the Association's designated inspection software to document findings
  • Send violation notices for observed compliance violations and close corrected violations, as directed


What you'll need:

  • Valid driver's license and reliable transportation
  • Ability to use a personal vehicle for inspections (mileage reimbursement provided)
  • Current auto insurance and vehicle registration
  • Strong attention to detail and ability to document findings accurately
  • Comfort using mobile devices, tablets, and inspection software


About Westward360:

Westward360 is dedicated to providing exceptional community management, rental management and brokerage services. Serving multiple markets throughout the United States, we have the systems, strategies, and expertise to meet the specialized needs of even the most demanding client. With more than 50,000 homes under management, we're your all-in-one real estate solution.

*Disability Notice: Disclosure is divulging or giving out personal information about a disability. It is important for the employee to provide information about the nature of the disability, the limitations involved, and how the disability affects the ability to learn and /or perform the job effectively. The employer has a right to know if a disability is involved when an employee asks for accommodations. Deciding if, when, and how to share disability-related information with a prospective or current employer can be overwhelming but we ask to please request a required accommodation prior to your first date of work. *Please note, a doctor's note may be requested by Human Resources, depending on the accommodation being requested, on a case-by-case basis.