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Independent Contractor Driver Jobs in Chicago, IL

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Independent Contractor Driver information

See Chicago, IL salary details

$406

$1.1K

$2.1K

How much do independent contractor driver jobs pay per week?

As of Sep 6, 2026, the average weekly pay for independent contractor driver 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 driver?

Independent contractor drivers are self-employed individuals who provide driving services to businesses or customers without being classified as employees. They often work for ride-sharing companies, delivery services, or freight transport, using their own vehicles and setting their own schedules. As independent contractors, they are responsible for their own taxes, insurance, and vehicle maintenance, and they may work for multiple companies at once. This role offers flexibility, but also requires more personal responsibility and business management than a traditional employee position.

What does an independent contractor driver do?

An independent contractor driver may work in delivery or personal transportation. If you work in freight or goods transportation, your duties are to determine the simplest route to make your deliveries, load and unload your vehicle, and fill out paperwork on behalf of your employer and the organization receiving goods. In human transportation, independent contractor drivers contract with companies and operate their own vehicles for fares, such as working for rideshare services. Your responsibilities include maintaining your vehicle, purchasing insurance, and maintaining a good driver rating.

How do independent contractor drivers typically manage fluctuating workloads and income variability?

Independent Contractor Drivers often experience fluctuating workloads and income due to factors like seasonal demand, market trends, and client schedules. To manage this variability, many drivers diversify their client base, schedule work in advance when possible, and budget carefully to account for leaner periods. Building strong relationships with reliable clients and using load boards or delivery platforms can also help secure more consistent assignments. Additionally, maintaining a well-organized schedule and proactively seeking new opportunities are key strategies for sustaining steady work as an independent contractor.

What is the difference between Independent Contractor Driver vs Delivery Driver?

AspectIndependent Contractor DriverDelivery Driver
CredentialsDriver's license, vehicle insurance, possibly a commercial licenseDriver's license, vehicle insurance
Work EnvironmentSelf-employed, flexible schedule, operates own vehicleEmployed by a company, fixed routes or schedules, company vehicle often provided
Employer & Industry UsageWorks independently across various industries like ride-sharing or freightWorks for companies like food delivery, parcel services, or courier companies

Independent Contractor Drivers typically operate as self-employed individuals with flexible schedules and their own vehicles, serving multiple industries. Delivery Drivers are usually employed by companies, follow set routes, and may use company vehicles. Both roles require a valid driver's license and insurance, but their employment structure and work environment differ significantly.

Is being an independent contractor driver worth it?

Being an independent contractor driver offers flexibility in scheduling and the potential for higher earnings based on hours worked and efficiency. However, it also involves managing your own expenses, insurance, and taxes, with income variability depending on demand and market conditions.
More about Independent Contractor Driver jobs

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

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

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

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

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

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

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

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

Independent Contractor Driver jobs near you
Infographic showing various Independent Contractor Driver job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 69% Full Time, 28% Part Time, and 2% Contract. Highlights an 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $58,399 per year, or $28.1 per hour.

Commercial Roofing Services - Independent Contractor Companies

City Wide Facility Solutions

Orland Park, IL • On-site

Contractor

Re-posted 21 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 selectively partnering with established Independent Contractors and service companies to service our commercial clients in the region. If you operate a structured business, deliver professional facility maintenance, restoration, or renovation services, and are looking for steady, recurring work - without the burden of chasing new contracts or managing collections - 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

We are selectively partnering with contractors who meet the following:

  • Proven experience in commercial roofing (required)
  • Proper licensing for commercial roofing work (as applicable)
  • General liability insurance and workers’ compensation coverage
  • Ability to assess, quote, and execute projects independently
  • Professional-grade equipment and crew
  • Strong communication and reliability
  • Commitment to safety, quality, and timelines

Preferred:

  • Experience working in occupied commercial or medical environments
  • Ability to provide clear documentation (photos, reports, scope clarity)
The Opportunity

ity Wide Facility Solutions is seeking a qualified commercial roofing contractor to support a current client project within our portfolio.

This is a project-based opportunity with the potential for ongoing work across multiple commercial properties, depending on performance, professionalism, and execution quality.

We manage a large base of commercial clients across office, medical, industrial, and institutional facilities. Our model is built around bringing vetted service providers into well-scoped, professionally managed opportunities—allowing contractors to focus on execution, not sales.

If you are looking to supplement your pipeline with well-defined commercial work and long-term partnership potential, this may be a strong fit.

If this is your company, keep reading.

INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:

  • Valid Business License (if necessary for the service type)
  • 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

The selected contractor will be responsible for delivering high-quality commercial roofing services, which may include:

  • Roof inspections and condition assessments
  • Leak detection and repair
  • Preventative maintenance
  • Partial or full roof replacement (as applicable)
  • Flat roof systems (TPO, EPDM, modified bitumen, etc.)
  • Proper documentation, reporting, and photo verification

Work will be performed in active commercial environments, requiring professionalism, coordination, and adherence to safety standards.

City Wide will:

  • Coordinate with the client
  • Define scope and expectations
  • Manage communication and administrative flow

You focus on:
???? Executing the work at a high level

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.
  • 20+ Other Opportunities
    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.