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Owner Operator Contractor Jobs in Illinois (NOW HIRING)

Clark Transfer Inc

CDL A Owner Operator

Oak Lawn, IL

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Waukegan, IL

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Aurora, IL

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

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Showing results 21-40

All JobsOwner Operator Contractor JobsOwner Operator Contractor Jobs in Illinois

Owner Operator Contractor information

What is an owner operator contractor?

Owner Operator Contractors are self-employed individuals or businesses who own and operate their own vehicles or equipment to provide transportation or delivery services. They typically contract with larger companies or clients to haul goods, manage logistics, or perform specialized tasks, often in the trucking or freight industry. As independent contractors, they are responsible for maintaining their equipment, managing expenses, and complying with regulations. This role offers greater flexibility and profit potential but also comes with higher risks and responsibilities compared to company-employed drivers.

What are some common challenges owner operator contractors face when managing their own business?

Owner Operator Contractors often face challenges related to balancing driving duties with the administrative responsibilities of running a business. Tasks such as handling contracts, maintaining equipment, managing finances, and securing consistent loads can require significant time and attention. Additionally, they are responsible for compliance with safety regulations and industry standards, which can be complex and ever-changing. Many find that building relationships with brokers and shippers is essential for steady work, and effective time management is key to maintaining profitability.

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

To thrive as an Owner Operator Contractor, you need a valid commercial driver's license (CDL), a clean driving record, and business management knowledge. Familiarity with electronic logging devices (ELDs), GPS systems, and compliance with Department of Transportation (DOT) regulations is essential. Strong organizational skills, self-motivation, and effective communication set top performers apart in managing routes and client relationships. These skills ensure safe, efficient operations and sustainable business growth in the competitive logistics industry.

What is the difference between Owner Operator Contractor vs Truck Driver?

AspectOwner Operator ContractorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCommercial Driver's License (CDL)
Work EnvironmentOwn truck, independent, flexible scheduleCompany-owned trucks, fixed routes, employer-managed
Employer/Industry UsageSelf-employed or contracted with carriersEmployed by trucking companies
Search/Comparison IntentHigh overlap in responsibilities and credentialsDifferent in independence and employment status

In summary, Owner Operator Contractors own and operate their trucks independently, often contracting with carriers, while Truck Drivers are typically employed by companies and operate company-owned vehicles. Both roles require a CDL, but their work setup and employment status differ significantly.

What are popular job titles related to Owner Operator Contractor jobs in Illinois?

For Owner Operator Contractor jobs in Illinois, the most frequently searched job titles are:

What job categories do people searching Owner Operator Contractor jobs in Illinois look for?

The top searched job categories for Owner Operator Contractor jobs in Illinois are:

Owner Operator Contractor jobs near you
Infographic showing various Owner Operator Contractor job openings in Illinois as of August 2026, with employment types broken down into 51% Full Time, 47% Part Time, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution.

CDL-A OWNER OPERATOR/INDEPENDENT CONTRACTORS

Freymiller

Chicago, IL • On-site

Contractor

Re-posted 3 days ago

Job description

CDL-A Owner Operator Jobs | Independent Contractor Opportunities

REAL Security. REAL Freight. REAL Pay.

Driver with Confidence. Partner with Freymiller.

Are you a CDL-A Owner Operator or Independent Contractor looking for: 

  • Steady miles 
  • High-paying freight 
  • Weekly pay
  • And a company that respects your time and hustle? 

At Freymiller, we offer consistent OTR freight, industry-leading fuel surcharge pay, and a network that supports your business like it's our own. 

NEW Pay Raise Just Dropped! 

  • Up to 70% Line Haul Revenue 
  • Fuel Surcharge - Ask Us How 
  • Big Sign-On Compensation! 
  • We Cover Travel to Orientation 
  • Paid Drop & Pick-Up 
  • Weekly Settlements = Fast Cash Flow 
  • Huge Fuel Discounts (Best in the Industry) 
  • Permits & Insurance? Covered under Our Authority 

You've Got Questions. We've Got Opportunities. 

Don't just drive- partner up. 

Apply Today and see what's possible with Freymiller!