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Flexible Container Owner Operator Jobs in Chicago, IL

At least 6 months of intermodal container or heavy equipment hauling experience preferred. * Clean ... Ability to work a flexible schedule, including nights, weekends, and holidays as needed.

Owner Operator Driver Altom Transport is a family-owned company built on trust, safety, and service ... Willing to work flexible schedules, including 24/7 operations if needed Benefits * Revenue & Fuel ...

Owner Operator Driver Altom Transport is a family-owned company built on trust, safety, and service ... Willing to work flexible schedules, including 24/7 operations if needed Benefits * Revenue & Fuel ...

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Owner Operator driver

Chicago, IL · On-site

$3.5K - $5.0K/wk

Our focus is on reliable communication, flexible dispatch, and consistent support for our contractors. Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

Be Seen First

Owner Operator driver

Chicago, IL · On-site

$3.5K - $5.0K/wk

Our focus is on reliable communication, flexible dispatch, and consistent support for our contractors. Owner-operators work with our 24/7 dispatch and tracking team while maintaining the freedom to ...

Freight mix: domestic containers, import/export intermodal rail, and depot moves in marine and ... This is the typical weekly range for owner operators running a full schedule -- before fuel ...

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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 Sep 7, 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 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 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 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 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:

Infographic showing various Flexible Container Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 26% Part Time, and 3% Contract. Highlights an 88% Physical, 2% Hybrid, and 10% Remote job distribution, with an average salary of $235,466 per year, or $113.2 per hour.

CDL A Owner Operator

ARL Network

Chicago, IL

$3.0K - $35K/wk

Full-time

Posted 17 days ago


Job description

Job Requirements:

•Valid Class A Commercial Driver's License (CDL-A).

•Minimum of 2 years of verifiable CDL-A driving experience.

•At least 6 months of intermodal container or heavy equipment hauling experience preferred.

•Clean Motor Vehicle Record (MVR) with a strong commitment to safe driving.

•Ability to pass a DOT physical, drug screening, and all pre-employment requirements.

•Knowledge of and commitment to DOT regulations and safety standards.

•Ability to work a flexible schedule, including nights, weekends, and holidays as needed.

•Familiarity with intermodal operations, rail terminals, and container yards is preferred.

•Strong communication skills and a professional, customer-focused attitude.

•Reliable, punctual, and able to work independently while collaborating with dispatch and operations.

Job Description:CDL-A OWNER OPERATOR – INTERMODAL? 70% OF LOAD REVENUEEarn $3,000–$3,500 Per Week After Fuel, Escrow & Deductions!Are you an experienced CDL-A Owner Operator looking for consistent freight, strong earningpotential, and a company that values your hard work? 24-7 Trucking Chicago is hiring dedicated CDL-A Owner Operators for consistent intermodal container work throughout the Chicago area and surrounding Midwest regions. We understand that Owner Operators are the backbone of our success. That's why we're committed to providing consistent opportunities, supportive dispatch, and the resources you need to keep your business moving.As an Owner Operator with 24-7 Trucking Chicago, you'll play a key role in keeping freight moving by safely transporting intermodal containers between major Chicago rail terminals, customer facilities, and our yard.  PAY & EARNING POTENTIAL70% of Load Revenue? Earn $3,000–$3,500 per week after fuel, escrow, and deductions? Local loads typically pay $350–$500? Regional loads typically pay $800–$1,200? Consistent, year-round intermodal freightPARKING LOCATIONS? Thornton, Illinois? Channahon, IllinoisWORK OUT OF MAJOR CHICAGO RAIL YARDSOur drivers work out of major Chicago-area rail terminals, including:? BNSF Elwood? NS Landers? CN Harvey? UP Global 4? CSX 59th Street? NS 47th StreetFREIGHT & LANES? Chicago local loads? Regional loads throughout Indiana, Wisconsin, and Iowa? Home daily on many lanes? No OTR? Opportunities for both local and regional freight? 20', 40', and 53' container opportunities? EQUIPMENT & SUPPORT? 60+ private chassis available? Private chassis help reduce delays and save valuable time? Day cab and sleeper opportunities available? Supportive dispatch and operations team? Consistent freight opportunities throughout the yearWHY DRIVE WITH 24-7 TRUCKING CHICAGO?? 70% of Load Revenue? Strong earning potential? $3,000–$3,500 weekly after fuel, escrow, and deductions? Consistent, year-round intermodal freight? Chicago local and regional opportunities? Home daily on many lanes? No OTR? Access to 60+ private chassis? Supportive dispatch and operations team? Opportunities for growth and long-term stability? A company that values and respects its Owner Operators. At 24-7 Trucking Chicago, we're committed to building long-term relationships with our driversand Owner Operators. We understand the importance of consistent work, reliable communication, and having a team behind you.KEY RESPONSIBILITIES? Safely operate a Class A commercial tractor while transporting intermodal containers between rail yards, customer facilities, and company locations.? Conduct thorough pre-trip and post-trip inspections to ensure the safe operation of equipment and compliance with DOT regulations.? Comply with all federal, state, and local traffic laws, DOT requirements, and company safety policies.? Maintain accurate electronic or paper logs, delivery records, and required shipping documentation.? Communicate professionally and effectively with dispatch, rail personnel, customers, and fellow team members.? Properly secure, inspect, and transport containers while following all intermodal handling and safety procedures.? Report equipment issues, delays, accidents, and safety concerns promptly to dispatch or management.? Provide exceptional customer service and represent 24-7 Trucking Chicago professionally at all pickup and delivery locations.? Work efficiently to meet pickup and delivery schedules while always prioritizing safety and compliance.? Maintain clean and organized equipment while promoting a culture of safety and teamwork.READY TO GROW YOUR BUSINESS?If you're an experienced CDL-A Owner Operator looking for consistent freight, competitive earnings, and a company that values your commitment, we'd love to hear from you. Join 24-7 Trucking Chicago and build your business with a team committed to your success. Apply today! Wage Range: $3000 per week - $35000 per week Weekly USDGeneral Description of Benefits: We offer programs designed to help support our Owner Operators, including:? Occupational Accident Insurance? Truck Insurance? Plate Program? IFTA Program? Buydown Program