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Independent Contractor Aggregate Owner Operator Jobs in Chicago, IL

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Independent Contractor Aggregate Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do independent contractor aggregate owner operator jobs pay per week?

As of Aug 16, 2026, the average weekly pay for independent contractor aggregate owner operator in Chicago, IL is $4,528.19, according to ZipRecruiter salary data. Most workers in this role earn between $2,476.92 and $6,734.62 per week, depending on experience, location, and employer.

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

AspectIndependent Contractor Aggregate Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business licensesCDL, possibly additional endorsements
Work EnvironmentOwn or lease trucks, operate independentlyWork for a company, follow company routes and schedules
Employer/Industry UsageSelf-employed or contracted in freight/logisticsEmployed by trucking companies or fleets
Search/Comparison IntentUnderstanding independent freight operationsUnderstanding company-employed driving roles

The main difference is that Independent Contractor Aggregate Owner Operators own or lease their trucks and operate independently, managing their own business. Truck Drivers typically work for a company, following their routes and schedules. Both roles require a CDL, but the owner-operator bears more responsibility for business management and expenses, while truck drivers focus on driving duties within a company's framework.

Is it better to be an owner-operator or an independent contractor?

For an independent contractor aggregate owner operator, being an owner-operator involves owning and operating your own vehicle, providing more control over schedules and routes but also requiring significant investment and responsibility. An independent contractor typically works for a company or as a freelancer, offering flexibility but less control over equipment and operations. The choice depends on your financial capacity, desired independence, and willingness to handle business management tasks.
Independent Contractor Aggregate Owner Operator jobs near you
Infographic showing various Independent Contractor Aggregate Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 33% Full Time, 27% Part Time, and 40% Contract. Highlights an 93% In-person, and 7% Remote job distribution, with an average salary of $235,466 per year, or $113.2 per hour.

Owner Operator Independent Contractor

Legacy Transportation

Chicago, IL • On-site

$200K - $300K/yr

Other

Posted 13 days ago

Job description

Legacy Transportation Services

Drive elite. Earn $200K–$300K+. Sign-on bonus $5000.00 first 6 months. Legacy Transportation Services is seeking experienced owner-operator independent contractor drivers to haul high-value, sensitive freight throughout all 48 states.

We partner with professional drivers who value precision, reliability, strong communication, and representing a premium carrier. If you are ready for specialized freight, consistent opportunity, and a company that respects your experience, this may be the right fit for you.

What you can earn:

  • $200,000–$300,000+ annual earning potential based on acceptance and completion of dispatched loads.
  • Earn up to a $5,000 earned onboarding bonus during your first 6 months
  • Compensation based on gross revenue and accepted loads
  • Use company trailer
  • Weekly pay
  • Flexible home time
  • Specialized, high-value freight
  • Partner with a respected, professional transportation company

Requirements:

Qualifications:

  • Valid Class A CDL
  • Current DOT Medical Card
  • Minimum 21 years of age
  • Own a CARB-compliant tractor eligible for California operations
  • Must be an owner-operator eligible to work as an independent contractor
  • Ability to run in all 48 states and Canada (if applicable)
  • Strong communication skills and punctuality
  • Willingness to live load/unload freight and secure freight inside trailer
  • Professional attitude and commitment to excellence

Ready to drive with the best? Call our recruiting team today: (408) 213-6345. Get your questions answered and take the next step toward building your future with Legacy. Take the wheel. Drive your success. Build your legacy with Legacy Transportation Services.

Apply