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Owner Operator Jobs in Chicago, IL (NOW HIRING)

STG Logistics

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

Owner Operator

Chicago, 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

Owner Operator

Chicago, 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

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 ...

Altom Transport, Inc

Owner Operator

Chicago, IL · On-site

Owner Operator Driver Altom Transport is a family-owned company built on trust, safety, and service. With over 10 strategic terminals and operations across 49 states and Canada, we specialize in the ...

JTS Logistics

Be Seen First

Truck Owner Operator

Gary, IN · On-site

$3.0K - $7.0K/wk

OWNER-OPERATOR OPPORTUNITY | JTS LOGISTICS Looking to maximize your earnings with a partner who has your back? JTS Logistics is hiring Owner-Operators with Sleeper-Semi Trucks (Dry Van). THE EARNINGS ...

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

Lisle, 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 ...

Atlas Logistics Inc.

Class A Owner Operator

Gary, IN

$260K - $312K/yr

Owner Operators are expected to operate with a strong commitment to safety, customer service, and on-time delivery while representing the Atlas brand. Responsibilities * Safely operate a Class A ...

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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

$664

$4.5K

$7.9K

How much do owner operator jobs pay per week?

As of Aug 13, 2026, the average weekly pay for owner operator in Chicago, IL is $4,531.63, according to ZipRecruiter salary data. Most workers in this role earn between $2,478.85 and $6,740.38 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.

Are owner operators making money?

Owner operators can make a profit depending on factors such as freight rates, operating costs, and efficiency. Successful owner operators typically manage expenses like fuel, maintenance, and insurance while securing consistent loads and maintaining good driving records. Earnings vary widely based on experience, routes, and market conditions.

What is an owner operator?

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.

What are 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 August 2026, with employment types broken down into 81% Full Time, 6% Part Time, and 13% Contract. Highlights an 100% In-person job distribution, with an average salary of $235,645 per year, or $113.3 per hour.

Owner Operator

STG Logistics

Joliet, IL • On-site

Full-time

Re-posted 19 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