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Independent Contractor Jobs in Chicago, IL (NOW HIRING)

MCSW Capital Enterprises LLC

Contractor

Chicago, IL · On-site

Independent Contractor Courier Driver - TForce Route MCSW Capital Enterprises LLC is seeking a reliable, professional Independent Contractor Courier Driver to operate a dedicated TForce Logistics ...

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Independent Contractor information

See Chicago, IL salary details

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$2.1K

How much do independent contractor jobs pay per week?

As of Sep 8, 2026, the average weekly pay for independent contractor in Chicago, IL is $1,123.06, according to ZipRecruiter salary data. Most workers in this role earn between $744.23 and $1,250.00 per week, depending on experience, location, and employer.

What is an independent contractor?

An Independent Contractor has a different type of employment agreement than a regular employee of a company. Independent Contractors are not guaranteed a steady paycheck. They cannot rely on their employer to provide all the materials and equipment needed to complete their work. The benefit to working as an Independent Contractor is that you have more control over how you conduct your work and the timeline for your projects. You must keep careful documentation for your taxes since you invoice clients for your work at an agreed rate and your clients do not pay payroll taxes or make any withholdings as they would for traditional employees.

What are the key skills and qualifications needed to thrive as an independent contractor, and why are they important?

To thrive as an Independent Contractor, you need strong expertise in your specific field, self-management abilities, and typically a business license or relevant credentials. Familiarity with project management tools, invoicing software, and contract management systems is often required. Outstanding communication, time management, and networking skills set successful independent contractors apart. These abilities are crucial for delivering high-quality work, maintaining client relationships, and sustaining a successful independent business.

How does an independent contractor typically manage client communication and project deadlines?

As an Independent Contractor, maintaining clear and timely communication with clients is essential for project success. Contractors often use a combination of email, project management tools, and scheduled meetings to keep clients updated on progress and address any concerns. Managing multiple projects simultaneously can be challenging, so setting realistic deadlines, tracking milestones, and proactively discussing any potential delays are important practices. By establishing clear expectations and regular check-ins, Independent Contractors can foster strong client relationships and ensure projects stay on track.

What is the difference between Independent Contractor vs Freelance Writer?

AspectIndependent ContractorFreelance Writer
CredentialsVaries by industry, often requires specific certifications or licensesTypically requires strong writing skills, portfolio, and possibly a degree in related field
Work EnvironmentOften works independently, may contract with multiple clientsWorks independently, usually on a project basis for various clients
Employer & Industry UsageUsed across many industries including construction, IT, consultingCommon in media, marketing, publishing, and content creation

While both Independent Contractors and Freelance Writers work independently and contract with clients, Independent Contractors often operate across various industries and may require industry-specific credentials. Freelance Writers focus on content creation, typically needing strong writing skills and portfolios. Both roles offer flexibility but differ in industry application and credential requirements.

What do I do as an independent contractor?

As an independent contractor, you provide services to clients or companies on a contractual basis, often working independently rather than as an employee. You are responsible for managing your own schedule, taxes, and equipment, and may need to obtain relevant licenses or certifications depending on the industry. Successful contractors typically communicate clearly, meet deadlines, and deliver quality work to maintain client relationships.
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What job categories do people searching Independent Contractor jobs in Chicago, IL look for?

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

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

Independent Contractor jobs near you
Infographic showing various Independent Contractor job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 18% Part Time, and 7% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $58,399 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 23 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