ZipRecruiter

Log In

1

Independent Contractor Insurance Jobs in Chicago, IL

previous pagenext page

Showing results 21-40

All JobsIndependent Contractor Insurance JobsIndependent Contractor Insurance Jobs in Chicago, IL

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 6, 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 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 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 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 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $58,353 per year, or $28.1 per hour.

Janitorial Independent Contractor - Companies not Individuals

City Wide Facility Solutions

Frankfort, IL • On-site

Full-time

Re-posted 20 days ago

Job description

Description

City Wide Facility Solutions is the largest management company in the building maintenance industry. We secure and manage commercial contracts and partner with skilled independent contractors to perform the work. We handle the sales, client communication, billing, and collections - so you can focus on doing what you do best.

We are currently looking for established Independent Contractors to service our commercial clients in Janitorial and specialty trades (Handyman, HVAC, Electrical, Plumbing, Pressure Washing, and more). If you have a structured business and want steady, recurring work without chasing new contracts or unpaid invoices, this may be a strong fit.

City Wide helps you grow your revenue, keep your crews busy, and get paid consistently - including guaranteed payment on the 10th for work performed.

We operate throughout South Chicagoland and Northwest Indiana - a strong commercial market with warehouses, medical facilities, manufacturing sites, schools, and municipal buildings.

For more information, contact Sandra Rivas at 708-365-8535 or chicagoshores-ic@gocitywide.com.

Requirements

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License
  • Worker's Compensation Insurance
  • General Liability Insurance
  • Federal EIN #
  • Other verifiable business
  • 18 years of age minimum
  • Favorable background investigation results
  • You can not be a sole proprietor

Benefits

We help you grow a real business - not just pick up extra work.

  • Consistent, Recurring Contracts (No Hunting Required)
    We bring you qualified commercial accounts so you can focus on operations - not cold calling, bidding, or chasing leads.
  • Reliable, On-Time Payments
    Eliminate collections headaches. We handle billing and client payment - you get paid consistently and predictably.
  • Scale Your Revenue Quickly
    Access multiple accounts across our territory - grow from a small crew to a multi-team operation with steady work.
  • Professional Account Management Support
    Our Facility Solutions Managers handle client communication, inspections, and issue resolution - helping you retain accounts and maintain high standards.
  • No Sales, No Admin Burden
    We manage contracts, client expectations, and service coordination - freeing you to focus on delivering quality work and building your team.
  • Opportunities Beyond Janitorial
    Expand into additional services (floor care, porter services, consumables, specialty cleaning) and increase revenue per account.
  • Long-Term Partnership Model
    We are invested in your growth - many of our partners have scaled into six-figure and multi-crew businesses with us.

Apply