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Owner Operator Jobs in Chicago, IL (NOW HIRING)

Logix Transportation

CDL A Owner Operator

Gary, IN

$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.

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

$4.0K - $7.5K/wk

26ft Box Truck Owner-Operator - OTR - 100% Load Rate - Weekly Pay. Arsen Trucking LLC is actively onboarding dependable independent contractor owner-operators for reliable Over-The-Road (OTR) freight ...

New World Van Lines

CDL A Owner Operator

Chicago, IL · On-site

We are seeking a skilled and reliable CDL Class A Owner Operator to join our team at New World Van Lines. As a crucial member of the New World Van Lines team, this position will be responsible for ...

STG Logistics

CDL A - 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

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

$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 ...

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Showing results 41-60

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 15, 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

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The most popular types of Owner Operator jobs in Chicago, IL are:

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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 Wanted - Home Nightly!

STG Logistics

Chicago, IL • On-site

Full-time

Re-posted 21 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