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Independent Contractor Insurance Jobs in Chicago, IL

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Independent Contractor Insurance information

See Chicago, IL salary details

$406

$1.1K

$2.1K

How much do independent contractor insurance jobs pay per week?

As of Aug 22, 2026, the average weekly pay for independent contractor insurance in Chicago, IL is $1,122.17, according to ZipRecruiter salary data. Most workers in this role earn between $742.31 and $1,248.08 per week, depending on experience, location, and employer.

What is an independent contractor insurance?

An Independent Contractor Insurance job involves helping self-employed individuals or freelancers secure the right insurance coverage to protect their businesses. This can include general liability, professional liability, workers' compensation, and other policies tailored to their specific industry. Insurance professionals in this role assess risks, recommend policies, and guide clients through the coverage selection process. They may work independently or for an insurance agency, ensuring contractors have the financial protection needed to operate safely and legally.

What skills and qualifications are needed for independent contractor insurance?

To excel as an Independent Contractor Insurance professional, you need a thorough understanding of insurance products, industry regulations, and self-employment management, often backed by appropriate state licensure or credentials. Familiarity with CRM platforms, e-signature tools, and quoting software is vital for managing client accounts and processing insurance applications efficiently. Strong communication, organizational skills, and an entrepreneurial mindset set top performers apart in this field. These abilities help build trust with clients, secure new business, and sustain a successful independent practice.

What are common challenges faced by independent contractor insurance professionals?

Independent Contractor Insurance professionals often face challenges such as sourcing their own clients, managing unpredictable income streams, and staying updated on constantly changing insurance regulations. They typically balance multiple client accounts and must be proactive in networking and marketing their services to build a steady book of business. Working independently also requires self-motivation and discipline, as success is largely determined by the effort you put into client outreach and relationship management. However, the role offers flexibility and the potential for significant earnings growth as you establish a strong client base.

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

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

What are popular job titles related to Independent Contractor Insurance jobs in Chicago, IL?

For Independent Contractor Insurance jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Independent Contractor Insurance jobs in Chicago, IL look for?

The top searched job categories for Independent Contractor Insurance jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Independent Contractor Insurance jobs?

Cities near Chicago, IL with the most Independent Contractor Insurance job openings:

Independent Contractor Insurance jobs near you
Infographic showing various Independent Contractor Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 37% Full Time, 20% Part Time, 4% Temporary, and 39% Contract. Highlights an 88% In-person, and 12% Remote job distribution, with an average salary of $58,353 per year, or $28.1 per hour.

Independent Contractor - Janitorial Services

City Wide Facility Solutions

Riverdale, IL • On-site

Contractor

Re-posted 15 days ago

Job description

City Wide Facility Solutions is the largest management company in the building maintenance industry, facilitating janitorial and over 20 additional maintenance services for various clients. We go beyond merely managing maintenance services for commercial facilities; we are committed partners who help save time and solve problems!

We are currently seeking Janitorial Independent Contractors to assist in meeting the needs of our clients. Partnering with City Wide can help your business grow, allowing you to concentrate on delivering quality service instead of focusing on sales and account collection, ultimately increasing your income.

If you are interested in joining our network as an independent contractor, please apply to this posting.

Requirements

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License (LLC or Inc)
  • Active Worker's Compensation Insurance
  • General Liability Insurance and Non-Owned Auto Coverage
  • Federal EIN #
  • Verifiable references
  • Must be at least 18 years of age
  • Favorable background investigation results
  • Must not be a sole proprietor

Benefits

This is a contract position and not benefits eligible.

Apply