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Freight Owner Operator Jobs in Chicago, IL (NOW HIRING)

STG Logistics

CDL A - Owner Operator

Joliet, IL · On-site

Chicago Owner-Operators Needed for Intermodal & Drayage Freight $2,000 Sign On Bonus! Text APPLY to (860) 300-2110 to get your quick app started! STG Drayage is growing its intermodal and drayage ...

STG Logistics

CDL A - Owner Operator

Mccook, IL · On-site

Chicago Owner-Operators Needed for Intermodal & Drayage Freight $2,000 Sign On Bonus! Text APPLY to (860) 300-2110 to get your quick app started! STG Drayage is growing its intermodal and drayage ...

Arsen Trucking

26ft Box Truck Owner-Operator

Chicago, IL · Remote

$4.0K - $7.5K/wk

Arsen Trucking LLC is actively onboarding dependable independent contractor owner-operators for reliable Over-The-Road (OTR) freight throughout all 48 states. Enjoy complete schedule freedom, no ...

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Showing results 21-40

All JobsFreight Owner Operator JobsFreight Owner Operator Jobs in Chicago, IL

Freight Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do freight owner operator jobs pay per week?

As of Aug 8, 2026, the average weekly pay for freight 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 are some common challenges freight owner operators face when managing their own business?

Freight Owner Operators often face challenges such as fluctuating fuel prices, securing consistent loads, and managing maintenance costs for their vehicles. Balancing operational expenses with competitive rates can be demanding, especially when working independently. Additionally, Owner Operators are responsible for handling their own bookkeeping, compliance with regulations, and maintaining a steady client base, which requires strong organizational and networking skills. Staying up to date with industry changes and cultivating good relationships with brokers and shippers can help mitigate some of these challenges.

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

To thrive as a Freight Owner Operator, you need a valid commercial driver's license (CDL), strong logistics knowledge, and experience with freight transportation regulations. Familiarity with electronic logging devices (ELDs), route planning software, and maintenance scheduling systems is typical, along with relevant trucking certifications. Strong time management, self-motivation, and customer service skills help build client relationships and ensure timely deliveries. These skills and qualities are vital for maximizing efficiency, maintaining safety standards, and growing a successful independent trucking business.

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

AspectFreight Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCommercial Driver's License (CDL)
Work EnvironmentOwns or leases truck, manages routes, flexible scheduleWorks for a company, follows company routes and schedules
Employer/Industry UsageIndependent contractor in freight/logisticsEmployee of a carrier or logistics company

Freight Owner Operators typically own or lease their trucks, manage their routes, and operate as independent contractors. In contrast, Truck Drivers are usually employed by a company, following set routes and schedules. Both roles require a CDL, but Owner Operators handle their business operations, offering more flexibility but also more responsibility.

What is a freight owner operator?

Freight Owner Operators are independent truck drivers or business owners who own and operate their own commercial vehicles to transport goods for clients. Unlike company drivers, they are not employees of a trucking company but contract their services to shippers or freight brokers. They handle their own business operations, including maintenance, fuel, insurance, and finding loads to haul. This role offers greater autonomy and potential for higher earnings but also comes with more responsibility and risk.
What are popular job titles related to Freight Owner Operator jobs in Chicago, IL? For Freight Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Freight Owner Operator jobs in Chicago, IL look for? The top searched job categories for Freight Owner Operator jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Freight Owner Operator jobs? Cities near Chicago, IL with the most Freight Owner Operator job openings:
Freight Owner Operator jobs near you
Infographic showing various Freight Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 40% Full Time, 58% Part Time, 1% Contract, and 1% Nights. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $235,466 per year, or $113.2 per hour.

CDL A - Owner Operator

STG Logistics

Joliet, IL • On-site

Full-time

Re-posted 14 days ago

Job description

Chicago Owner-Operators Needed for Intermodal & Drayage Freight

$2,000 Sign On Bonus! 


Text APPLY to (860) 300-2110 to get your quick app started!

STG Drayage is growing its intermodal and drayage network and looking to contract with experienced Owner-Operators in Chicago, IL and surrounding port and rail markets.

If you’re looking for consistent container freight, competitive rates, and a local team that understands port and rail operations, STG Drayage has opportunities ready now.

Why Owner-Operators Choose STG Drayage

  • $2,000 Sign On Bonus
  • Home Nightly 
  • Consistent Port & Rail Freight
  • Competitive Weekly Settlements
  • Local & Regional Drayage Runs
  • Drop & Hook Opportunities
  • Industry-Leading Fuel Discounts
  • Expanding Freight Network Across Major Ports & Rail Ramps
  • Supportive Local Team

Built for Intermodal Drivers

STG Drayage is one of North America’s fastest-growing intermodal carriers because it understands what matters most to owner-operators: steady freight, efficient turns, strong communication, and maximizing your time on the road.

Whether you’re running port containers daily or looking to grow your intermodal business, STG Drayage offers long-term opportunity with consistent freight volumes.

Owner-Operator Requirements

  • Minimum 21 Years Old
  • 12+ Months of Verifiable Tractor-Trailer Experience Within the Last 5 Years
  • Military driving experience may qualify toward road experience requirements (call for details)

If you’re a safety-focused owner-operator looking for consistent drayage or intermodal freight, partner with STG Drayage today.

Call now to get started!

Apply