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Local Owner Operator Jobs in Chicago, IL (NOW HIRING)

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 ...

ARL Network

CDL A Owner Operator Intermodal

Joliet, IL

$2.5K - $3.5K/wk

General Express, a proud division of ARL Transport has Local Home Daily Intermodal Owner Operator positions in Joliet IL and surrounding areas . For any questions, please feel free to contact the ...

ARL Network

CDL A Owner Operator Intermodal

Chicago, IL

$2.5K - $3.5K/wk

General Express, a proud division of ARL Transport has Local Home Daily Intermodal Owner Operator positions in Joliet IL and surrounding areas . For any questions, please feel free to contact the ...

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Showing results 21-40

All JobsLocal Owner Operator JobsLocal Owner Operator Jobs in Chicago, IL

Local Owner Operator information

See Chicago, IL salary details

$664

$4.5K

$7.9K

How much do local owner operator jobs pay per week?

As of Aug 11, 2026, the average weekly pay for local 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 are some common challenges faced by local owner operators, and how can they be managed?

Local Owner Operators often encounter challenges such as managing fluctuating fuel costs, maintaining their vehicles, and balancing administrative tasks with driving responsibilities. Since they typically operate independently, they must also navigate securing consistent loads and building strong relationships with local clients. Staying organized, regularly maintaining equipment, and leveraging load boards or working with reliable brokers can help address these challenges and ensure steady business. Networking with other operators and staying informed about local regulations can also provide valuable support.

What are the key skills and qualifications needed to thrive as a local owner operator, and why are they important?

To thrive as a Local Owner Operator, you need a commercial driver's license (CDL), a clean driving record, business acumen, and knowledge of local routes and regulations. Familiarity with fleet management software, electronic logging devices (ELDs), and truck maintenance tools is typically required. Strong time management, self-motivation, and customer service skills help you excel in this role. These skills ensure safe, efficient deliveries, compliance with regulations, and the successful operation of your independent trucking business.

How do local owner operators find jobs?

Local owner operators find jobs through load boards, broker networks, and direct relationships with shippers or carriers. Building a strong reputation, maintaining proper licensing and insurance, and utilizing industry-specific tools can help secure consistent work and better freight opportunities.

What is the difference between Local Owner Operator vs Local Truck Driver?

AspectLocal Owner OperatorLocal Truck Driver
CredentialsCommercial Driver's License (CDL), vehicle ownershipCDL, no vehicle ownership
Work EnvironmentOperates own or leased truck within local routesDrives company-owned trucks within local routes
Employer & Industry UsageIndependent contractor or small fleet owner in freight/logisticsEmployee of a trucking company or carrier
Search & Comparison IntentYesNo

In summary, a Local Owner Operator owns and operates their own truck, often working independently or as part of a small fleet, while a Local Truck Driver typically works as an employee for a company, driving company-owned trucks within local routes. Both roles require a CDL, but ownership and employment status differ significantly.

What is a local owner operator?

A Local Owner Operator is a self-employed truck driver who owns and operates their own vehicle, typically working within a specific geographic region or city rather than long-haul routes. They contract with companies or freight brokers to transport goods locally, allowing for more predictable schedules and regular home time. As business owners, they are responsible for maintaining their trucks, managing expenses, and complying with all relevant regulations. Many local owner operators enjoy the independence and flexibility the role provides.
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 Local Owner Operator jobs in Chicago, IL? For Local Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Local Owner Operator jobs in Chicago, IL look for? The top searched job categories for Local Owner Operator jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Local Owner Operator jobs? Cities near Chicago, IL with the most Local Owner Operator job openings:
Local Owner Operator jobs near you
Infographic showing various Local 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 96% Physical, 1% Hybrid, and 3% Remote job distribution, with an average salary of $235,652 per year, or $113.3 per hour.

CDL A - Owner Operator

STG Logistics

Mccook, IL

Full-time

Re-posted 12 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