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Flexible Container Owner Operator Jobs in Chicago, IL

STG Logistics

Owner Operator

Joliet, IL

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 Logistics

Owner Operator

Chicago, IL

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 Logistics

Owner Operator

Chicago, IL

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 Logistics

Owner Operator

Mccook, IL · On-site

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 Logistics

CDL A - Owner Operator

Chicago, IL · On-site

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 Logistics

CDL A - Owner Operator

Joliet, IL · On-site

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 Logistics

CDL A - Owner Operator

Mccook, IL

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 ...

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All JobsContainer Owner Operator JobsFlexible Container Owner Operator JobsFlexible Container Owner Operator Jobs in Chicago, IL

Flexible Container Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do flexible container owner operator jobs pay per week?

As of Aug 10, 2026, the average weekly pay for flexible container 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 the difference between Flexible Container Owner Operator vs Drayage Driver?

AspectFlexible Container Owner OperatorDrayage Driver
CredentialsCommercial Driver's License (CDL), experience with container haulingCDL, often specialized in port or terminal operations
Work EnvironmentIndependent, on the road, hauling containers across regionsPort terminals, intermodal yards, short-distance hauls
Employer & IndustryOwner-operators, freight carriers, logistics companiesPort authorities, shipping lines, intermodal companies

The main difference is that Flexible Container Owner Operators typically operate independently hauling containers over longer distances, while Drayage Drivers focus on short-distance container moves within ports or terminals. Both roles require CDL licenses and involve container transportation, but their work environments and operational scopes differ.

What are the key skills and qualifications needed to thrive as a flexible container owner operator?

To thrive as a Flexible Container Owner Operator, you need a valid commercial driver's license (CDL), experience with freight logistics, and knowledge of transportation regulations. Familiarity with route planning software, GPS navigation systems, and electronic logging devices (ELDs) is typically required. Strong organizational skills, self-motivation, and effective communication help operators manage schedules, client relationships, and on-the-road challenges. These skills and qualifications are essential for ensuring safe, efficient deliveries and maintaining a successful independent logistics business.

What are some common challenges faced by flexible container owner operators and how can they be managed?

Flexible Container Owner Operators often encounter challenges such as fluctuating freight demand, maintaining their equipment, and managing operational costs like fuel and insurance. Navigating varying schedules and securing consistent loads can also be demanding, especially when working independently. Building strong relationships with shippers and logistics companies, staying on top of preventative maintenance, and using load boards or dispatch services can help mitigate these challenges and ensure a smoother workflow.

What is a flexible container owner operator?

A Flexible Container Owner Operator is an independent contractor who owns and operates their own vehicle or fleet, specializing in the transportation of flexible containers such as bulk bags, intermediate bulk containers (IBCs), or other collapsible packaging. They partner with logistics companies or shippers to move goods efficiently and often have control over their schedule and routes. This role requires strong knowledge of transport regulations, container handling, and often involves both local and regional deliveries. It is ideal for entrepreneurs in the logistics industry seeking flexibility and independence.
What are popular job titles related to Flexible Container Owner Operator jobs in Chicago, IL? For Flexible Container Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Flexible Container Owner Operator jobs in Chicago, IL look for? The top searched job categories for Flexible Container Owner Operator jobs in Chicago, IL are:
Flexible Container Owner Operator jobs near you
Infographic showing various Flexible Container Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $235,466 per year, or $113.2 per hour.

Owner Operator

STG Logistics

Joliet, IL

Full-time

Re-posted 16 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