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Owner Operator Jobs in Chicago, IL (NOW HIRING)

STG Logistics

Owner Operator

Chicago, IL

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

Owner Operator

Joliet, IL

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

Owner Operator

Chicago, IL

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

Owner Operator

Mccook, IL

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 ...

J.B. Hunt Transport

Owner Operator Truck Driver

Worth, IL · On-site

$202K/yr

Hunt has owner operator jobs available! Contract with J.B. Hunt Highway Services and gain access to one of the largest freight bases in the country, providing you with the compensation you want and ...

J.B. Hunt Transport

Owner Operator Truck Driver

Gary, IN · On-site

$202K/yr

Hunt has owner operator jobs available! Contract with J.B. Hunt Highway Services and gain access to one of the largest freight bases in the country, providing you with the compensation you want and ...

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Showing results 1-20

All JobsOwner Operator JobsOwner Operator Jobs in Chicago, IL

Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do owner operator jobs pay per week?

As of Jul 27, 2026, the average weekly pay for 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 Does an Owner-Operator Do?

The term Owner-Operator refers to a trucking professional who owns their truck and drives it as an independent contractor. Many companies hire independent operators to haul goods for them. Using contractors allows construction companies to keep pace with the rise and fall of demand for their products without the overhead cost of maintaining a fleet of vehicles that may be insufficient in one season and excessive in another. Owner-Operators need to hold a Commercial Driver's License (CDL) in the class that allows them to drive their vehicle and have sufficient training in operating and maintaining the machine. They can choose their own schedule and pick which jobs to take.

What are the key skills and qualifications needed to thrive as an Owner Operator, and why are they important?

To thrive as an Owner Operator, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in truck driving and logistics. Familiarity with fleet management software, GPS navigation systems, and compliance tools like electronic logging devices (ELDs) is essential. Excellent time management, business acumen, and customer service skills help set top performers apart in this role. These skills and qualities are crucial for ensuring safe, efficient operations and building a successful, profitable transportation business.

What company in Texas is paying truckers $14000 a week?

Owner operators in trucking can sometimes earn up to $14,000 a week depending on factors like freight type, routes, and experience. Such high earnings are typically associated with specialized or high-demand loads, and drivers often work long hours or on dedicated routes. It's important to verify company offers and ensure compliance with industry standards and regulations.

What are Owner Operators?

Owner operators are independent truck drivers or small business owners who own and operate their own commercial vehicles. They either lease their services to larger freight carriers or contract directly with clients to transport goods. Unlike company drivers, owner operators are responsible for managing their own business expenses, such as fuel, maintenance, insurance, and taxes. This role offers more autonomy and the potential for higher earnings, but it also comes with greater financial risk and responsibility.

What is the difference between Owner Operator vs Truck Driver?

AspectOwner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving license
Work EnvironmentOwn truck, self-managed scheduleCompany-owned trucks, set schedules
EmployerSelf-employed or independent contractorEmployers or carriers
Work FlexibilityHigh, controls own routes and hoursLimited, dictated by employer

Owner Operators own and operate their trucks, managing their own schedules and business. Truck Drivers typically work for a company, following set routes and schedules. The main difference lies in independence and business ownership, with Owner Operators having more control but also more responsibilities.

Is being an owner-operator still worth it?

Owner-operators in trucking can still be profitable, but success depends on factors like freight rates, fuel costs, and equipment expenses. It requires strong business management skills, reliable equipment, and the ability to adapt to market fluctuations to maintain profitability.

Why do most people quit trucking?

Many owner operators quit trucking due to long hours, high operating costs, and inconsistent income. The demanding schedule and the need for strong driving skills can also contribute to job dissatisfaction and burnout.

Is there a $7500 tax credit for truck drivers?

There is no specific $7,500 tax credit exclusively for truck drivers. However, owner operators and commercial drivers may qualify for various tax deductions related to vehicle expenses, equipment, and business costs, which can reduce taxable income. It's advisable to consult a tax professional for personalized guidance on available credits and deductions based on individual circumstances.

What are some common challenges Owner Operators face when managing their own trucking business?

Owner Operators often encounter challenges such as maintaining cash flow, managing fluctuating fuel costs, and ensuring their vehicles are properly maintained to avoid unexpected downtime. Balancing administrative tasks—like scheduling, invoicing, and compliance—with time on the road can also be demanding. Building relationships with reliable clients or brokers and navigating complex regulations are crucial for long-term success. Staying organized and proactive in handling these responsibilities helps Owner Operators thrive in a competitive industry.
More about Owner Operator jobs
What are the most commonly searched types of Owner Operator jobs in Chicago, IL? The most popular types of Owner Operator jobs in Chicago, IL are:
What are popular job titles related to Owner Operator jobs in Chicago, IL? For Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Owner Operator jobs in Chicago, IL look for? The top searched job categories for Owner Operator jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Owner Operator jobs? Cities near Chicago, IL with the most Owner Operator job openings:
Owner Operator jobs near you
Infographic showing various Owner Operator job openings in Chicago, IL as of July 2026, with employment types broken down into 73% Full Time, 9% Temporary, and 18% Contract. Highlights an 100% In-person job distribution, with an average salary of $235,652 per year, or $113.3 per hour.
Owner Operator

Owner Operator

STG Logistics

Chicago, IL

Full-time

Posted 2 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