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Local Class A Owner Operator Jobs in Chicago, IL

Medline

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Local Class A Driver

Grayslake, IL · On-site

$29/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

Usora Express LLC

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CDL-A Owner Operator OTR | Earn $8,000-$12,000 Gross Weekly

Chicago, IL · On-site

$260K - $416K/yr

Trailer rental options available through local partners Transparent Costs We believe in being ... Class A CDL required * Minimum 2 years OTR experience * Must own a sleeper cab truck (2015 or newer ...

Usora Express LLC

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CDL-A Owner Operator OTR | Earn $8,000-$12,000 Gross Weekly

Joliet, IL · On-site

$260K - $416K/yr

Trailer rental options available through local partners Transparent Costs We believe in being ... Class A CDL required * Minimum 2 years OTR experience * Must own a sleeper cab truck (2015 or newer ...

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Medline

Local Class A Driver

Grayslake, IL · On-site

$26.75 - $38.75/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

Medline

Local Class A Driver

Grayslake, IL · On-site

$26.75 - $38.75/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

Medline

Local Class A Driver

Grayslake, IL · On-site

$26.75 - $38.75/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

Medline

Local Class A Driver

Grayslake, IL · On-site

$26.75 - $38.75/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

Medline

Local Class A Driver

Grayslake, IL

$26.75 - $38.75/hr

The Driver is responsible for operating a Class A vehicle to transport life-saving medical products to our local customers. The Driver plays a critical role in building positive relationships with ...

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Showing results 21-40

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

Local Class A Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do local class a owner operator jobs pay per week?

As of Aug 8, 2026, the average weekly pay for local class a 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 are the key skills and qualifications needed to thrive as a local Class A owner operator?

To excel as a Local Class A Owner Operator, you need a valid Class A Commercial Driver’s License (CDL), a clean driving record, and knowledge of DOT regulations. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and basic truck maintenance tools is typically required. Strong time management, self-motivation, and customer service skills help build client relationships and ensure on-time deliveries. These competencies are vital for maintaining safety, efficiency, and business profitability in local freight operations.

What is the difference between Local Class A Owner Operator vs Local Company Driver?

AspectLocal Class A Owner OperatorLocal Company Driver
CredentialsCommercial Driver's License (CDL) Class A, permits for haulingCDL Class A, often with company-specific training
Work EnvironmentIndependent, self-managed routes, often on own equipmentEmployed by a company, assigned routes, using company trucks
Employer & Industry UsageFreight, logistics, trucking companies, independent contractingSame industries, employed directly by carriers

In summary, Local Class A Owner Operators operate their own trucks and manage their routes independently, while Local Company Drivers work for a trucking company using company-owned equipment. Both roles require a CDL Class A license and serve similar industries, but differ mainly in equipment ownership and employment structure.

What is a local Class A owner operator?

A Local Class A Owner Operator is a professional truck driver who owns and operates their own commercial vehicle (usually a tractor-trailer) and holds a Class A Commercial Driver’s License (CDL). They typically contract with transportation companies or find their own freight, focusing on local or regional routes that allow them to return home daily or frequently. As independent business owners, they are responsible for managing their business operations, vehicle maintenance, and compliance with safety regulations. This role offers more autonomy compared to company drivers but also comes with the responsibility of handling all business-related expenses and logistics.

What are some common challenges faced by local Class A owner operators, and how can they be managed effectively?

Local Class A Owner Operators often face challenges such as managing their own schedules, maintaining their vehicles, and ensuring consistent work through contracts or freight brokers. Balancing time on the road with administrative tasks like invoicing and compliance paperwork can also be demanding. Effectively managing these challenges involves strong organizational skills, building reliable relationships with shippers or dispatchers, and staying proactive with vehicle maintenance to avoid unexpected downtime. Many operators find that joining reputable carrier networks or leveraging load boards helps secure steady work while allowing them to maintain some independence.
What are popular job titles related to Local Class A Owner Operator jobs in Chicago, IL? For Local Class A Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Local Class A Owner Operator jobs in Chicago, IL look for? The top searched job categories for Local Class A Owner Operator jobs in Chicago, IL are:
Local Class A Owner Operator jobs near you
Infographic showing various Local Class A Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 68% Full Time, 28% Part Time, and 3% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $235,466 per year, or $113.2 per hour.

CDL-A Owner Operator Truck Driver in Chicago , IL

UniGroup Drivers

Chicago, IL • On-site

$220K/yr

Full-time

Posted 16 days ago

Job description

UniGroup, the parent company of both Mayflower and United, has exciting Class A owner operator jobs open now! Join the nation's leader in specialized products transport and grow your CDL-A truck driving business where you want with 600 locations nationwide.
BENEFITS:
  • Average annual salary $220k
  • Take PRIDE in hauling high value electronics, special commodities
  • Out 2-3 weeks
  • 100% Accessorial & Fuel Surcharge paid to you!
  • Fuel wherever you want with .30-.34 cents per gallon average fuel discounts!
  • Driver Referral Program
  • 24/7 roadside assistance available
  • Passenger authorization program
  • Plate and permit program
  • Reimbursed for truck washes (1 per month)
  • Tire discount program

REQUIREMENTS:
  • Valid Class 'A' CDL
  • Currently own a tractor and willing to handle freight
  • One year, preferred, verifiable over-the-road, tractor-trailer driving experience.
  • Must pass all company and DOT requirements, including MVR, PSP report, DOT medical screen, pre-qualification drug screen and criminal background investigation
  • Age 21 years or older
  • Seeking safe, quality minded and customer service-oriented

Apply