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Remote Insurance Inspector Jobs in Chicago, IL (NOW HIRING)

Pioneer Agency

Insurance Agent

Chicago, IL · Remote

$50K - $75K/yr

Remote work opportunities with flexible scheduling to fit your lifestyle. * Competitive commission ... No prior insurance experience is necessary; training will be provided. Work Location: Remote ...

Pioneer Agency

Insurance Agent

Chicago, IL · Remote

$50K - $75K/yr

Remote work opportunities with flexible scheduling to support work-life balance. * Competitive ... No prior insurance experience or license required; training provided. Prior sales or client-service ...

Gallagher

Medicare Insurance Agent

Chicago, IL · Remote

$21/hr

YWI is hiring remote Medicare Sales Agents throughout the USA. We believe every candidate brings ... We provide paid insurance licensing to help you kick-start your career as a Medicare Consultant.

Big I Illinois

Insurance Agent

IL · On-site +1

$60K - $150K/yr

... remote position. Compensation: $60,000.00 - $150,000.00 per year YOUR FUTURE as an Independent ... Independent insurance agents protect our customers by providing home, auto, business, life and ...

Summers Agency

Insurance Agent - Work From Home

Chicago, IL · On-site +1

$70K - $125K/yr

Help Families Protect What Matters Most - Remote Role If you're looking for a career where you can ... grow within the insurance industry. In this role, you'll work with families who are actively ...

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Remote Insurance Inspector information

See Chicago, IL salary details

$11.3K

$60.2K

$135.5K

How much do remote insurance inspector jobs pay per year?

As of Jun 7, 2026, the average yearly pay for remote insurance inspector in Chicago, IL is $60,239.00, according to ZipRecruiter salary data. Most workers in this role earn between $36,437.00 and $75,441.00 per year, depending on experience, location, and employer.

What is a Remote Insurance Inspector job?

A Remote Insurance Inspector evaluates properties, businesses, or assets for insurance purposes without needing to visit in person. Using photos, videos, documents, and virtual tools, they assess risks, verify policy details, and ensure compliance with underwriting standards. This role often involves analyzing reports, communicating with policyholders, and collaborating with insurance companies. Strong attention to detail and knowledge of industry regulations are essential.

What does a typical workday look like for a Remote Insurance Inspector?

A typical day for a Remote Insurance Inspector involves scheduling and conducting inspections of properties—often by analyzing submitted photos and documentation, or occasionally performing virtual walk-throughs with clients. Inspectors review policies, evaluate risk factors, prepare detailed reports, and communicate findings to insurance companies and policyholders. Most work is performed independently, though collaboration with underwriting teams or claim adjusters may be required. Depending on the employer, you might handle a flexible workload and use online systems to organize tasks and submit your findings efficiently.

What are the key skills and qualifications needed to thrive in the Remote Insurance Inspector position, and why are they important?

To thrive as a Remote Insurance Inspector, you need a solid understanding of property and casualty insurance, attention to detail, and relevant field experience, often supported by an associate degree or industry certification. Familiarity with inspection software, digital cameras, and cloud-based reporting systems is essential for completing and submitting inspections remotely. Strong organizational skills, self-motivation, and effective communication are important soft skills that help in managing caseloads and interacting with clients. These skills ensure accurate assessments, timely reporting, and high-quality service in an independent, remote work environment.

What are the most commonly searched types of Insurance Inspector jobs in Chicago, IL? The most popular types of Insurance Inspector jobs in Chicago, IL are:
What are popular job titles related to Remote Insurance Inspector jobs in Chicago, IL? For Remote Insurance Inspector jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Insurance Inspector jobs in Chicago, IL look for? The top searched job categories for Remote Insurance Inspector jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Insurance Inspector jobs? Cities near Chicago, IL with the most Remote Insurance Inspector job openings:
Remote Insurance Inspector jobs near you
Infographic showing various Remote Insurance Inspector job openings in Chicago, IL as of May 2026, with employment types broken down into 56% Full Time, 19% Part Time, 19% Contract, and 6% Nights. Highlights an 87% In-person, and 13% Remote job distribution, with an average salary of $60,239 per year, or $29 per hour.

Commercial Vehicle Inspector (Remote)

Beacon Inspection

Chicago, IL • Remote

$65/hr

Contractor

Posted 7 days ago

Job description

Now Hiring Commercial Vehicle Inspectors. Enjoy the flexibility of setting your own schedule, and take charge of your day. Minimal supervision maximum independence!

This is a Contract/1099 position. You would be an independent contractor and paid a flat rate fee per inspection + mileage reimbursement.

The ideal candidate will have strong familiarity with trucks, trailers, and equipment. This experience may come from diesel technician or mechanical work, or from hands-on exposure to operating and inspecting heavy vehicles. Candidates with experience in related inspection fields, including auto, home, or insurance inspections, are also encouraged to apply. ASE Certification preferred.

Who We Are

Beacon Inspections is a US based inspection company with a large network of inspectors covering the entire continental US. Beacon Inspections offers fast, affordable, and accurate inspections with a focus on commercial trucks, trailers, and equipment.

Duties:

  • Flexible Schedule (daylight hours, Monday - Friday), ability to complete inspections in 48-72 hours
  • Schedule appt w/ on site contact provided to inspector
  • Start & Move Vehicle (to position to take pics and videos)
  • Check diagnostics (w/ heavy duty diagnostic scanner, OBD II, or on board screen)
  • Check for leaks and deficiencies
  • Tire & Brake Depths
  • 100+ photos
  • Film Video

Required:

  • Detail oriented and organized
  • Access to a newer smartphone or tablet with sufficient data plan
  • Proficiency with common operating systems (iOS, Google Chrome, Microsoft)
  • Access to a laptop/desktop computer
  • Heavy Duty Truck Diagnostic Scanner (must read fault codes, and provide printable or exportable report), OBD II, or willingness to purchase for required inspections
  • Tire Depth Gauge
  • Reliable vehicle and a valid driver's license

Perks:

  • Extra income with flexible, ad-hoc work
  • Accept the jobs you want
  • Ability to work with minimal guidance and supervision

Ad Focus: City