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

Logix Transportation

CDL A Owner Operator

Joliet, IL

$234K - $286K/yr

Owner Operators... Pay yourself FIRST with lightweight freight! Logix isn't your typical hauler. The freight we carry includes some of the most sensitive and valuable equipment this nation produces.

Arsen Trucking

26ft Box Truck Owner-Operator

Chicago, IL · Remote

$5.0K - $9.0K/wk

Arsen Trucking LLC is onboarding reliable 26ft Box Truck Owner-Operators to haul consistent OTR freight across the United States. This is an independent contractor opportunity with weekly pay, full ...

Logix Transportation

CDL A Owner Operator

Gary, IN · On-site

$234K - $286K/yr

Owner Operators... Pay yourself FIRST with lightweight freight! Logix isn't your typical hauler. The freight we carry includes some of the most sensitive and valuable equipment this nation produces.

Forward Air

CDL-A Owner Operator Driver

Elwood, IL · On-site

$4.1K - $5.2K/wk

MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to $250,000 gross per year* Why Drive for Forward Air? At Forward Air, Owner Operators aren't just drivers, they're ...

Forward Air

CDL-A Owner Operator Driver

Chicago, IL · On-site

$4.1K - $5.2K/wk

MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to $250,000 gross per year* Why Drive for Forward Air? At Forward Air, Owner Operators aren't just drivers, they're ...

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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 30, 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 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 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 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 42% Full Time, 56% 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.

Intermodal Trucking Owner Operator

Chicago, IL • On-site

TRANSOURCE LOGISTICS INC
See more jobs at TRANSOURCE LOGISTICS INCexternal

$3.5K - $6.0K/wk

Contractor

Re-posted 14 days ago

Job description

Transource Logistics is in search of owner operators to haul shipping containers out of Chicagoland terminals to the surrounding states. Position is daytime and may require early morning starts. Need 2 years verifiable tractor trailer experience. Intermodal experience is preferred but not required.
To apply, click the link https://intelliapp.driverapponline.com/m/3153721?r=ZipRecruiter
BENEFITS:
-HOME EVERY NIGHT
-FUEL CARDS
-DRIVER REFERRAL BONUS
-NO TOUCH FREIGHT
-CASH ADVANCES AVAILABLE
-WEEKLY DIRECT DEPOSIT