1

Owner Operators Jobs in Kentucky (NOW HIRING)

$118 - $141/hr

Contract | Owner Operator | Current as of Aug 24, 2026 CW Freight is looking to add experienced Owner Operators for local and regional intermodal work out of our Chicago operation. Description ...

Your safety is our top priority! Company Overview: RIDENROLL (www.RidenRoll.com) is a California-based, for-profit technology platform that connects users with ride-hauling drivers and delivery ...

$80 - $120/hr

We are seeking responsible, reliable, and motivated Owner Operators with their own Sprinter Van, Cargo Van, or Small Box Truck to join our rapidly growing transportation network. If you value ...

New

$80 - $120/hr

Contract | Owner Operator | Current as of Aug 19, 2026 Grow your trucking business with professional dispatch support. We work with CDL & Non-CDL Owner Operators and all truck types, including Dry ...

$150 - $190/hr

CDL-A Owner Operators - New 2027 Hoppers Run Your Truck. Let Us Handle the Rest. OWNER OPERATORS - OTR HOPPER You bring the truck - we handle the rest. What You Get: * High Percentage Pay + 100% Fuel ...

next page

Showing results 1-20

Owner Operators information

See Kentucky salary details

$559

$3.8K

$6.7K

How much do owner operators jobs pay per week?

As of Sep 5, 2026, the average weekly pay for owner operators in Kentucky is $3,817.77, according to ZipRecruiter salary data. Most workers in this role earn between $2,088.46 and $5,678.85 per week, depending on experience, location, and employer.

What is an owner operator?

An Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle. They either haul freight for a company under a contract or run their own independent trucking business. Responsibilities include managing expenses, securing contracts, maintaining their truck, and complying with industry regulations. Being an Owner Operator provides more control over routes and schedules but also comes with financial risks and business management responsibilities.

What are the key skills and qualifications needed to thrive as an owner operator?

To thrive as an Owner Operator, you need strong business management skills, a commercial driver's license (CDL), and a thorough understanding of transportation regulations and logistics. Familiarity with electronic logging devices (ELDs), freight brokerage platforms, and route planning software is often necessary. Excellent time management, self-motivation, and communication skills set standout candidates apart in this competitive field. These skills and qualities are vital to efficiently manage your own business, ensure regulatory compliance, and maintain reliable client relationships.

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

Owner Operators often encounter challenges such as fluctuating fuel costs, finding consistent loads, maintaining their vehicles, and keeping up with regulatory requirements. Staying organized with digital tools for load planning and maintenance scheduling can help streamline operations. Building strong relationships with freight brokers and direct shippers may increase access to steady work, while careful budgeting can assist in managing overhead expenses. Additionally, keeping up-to-date with industry regulations can ensure your business remains compliant and operates smoothly. Addressing these challenges proactively helps promote a successful and sustainable operation.

How do owner operators find jobs?

Owner operators find jobs through load boards, freight brokers, and direct relationships with shippers or carriers. They often use online platforms, industry networks, and maintain good communication to secure consistent work, while also managing necessary licenses and insurance requirements.

How much do most owner operators make?

Most owner operators earn between $100,000 and $200,000 annually, depending on factors such as experience, routes, and load types. Earnings can vary widely based on fuel costs, maintenance, and operational efficiency, with successful operators often managing their own schedules and equipment to maximize profit.

What are the most commonly searched types of Owner Operators jobs in Kentucky?

The most popular types of Owner Operators jobs in Kentucky are:

What are popular job titles related to Owner Operators jobs in Kentucky?

For Owner Operators jobs in Kentucky, the most frequently searched job titles are:

What cities in Kentucky are hiring for Owner Operators jobs?

Cities in Kentucky with the most Owner Operators job openings:

Infographic showing various Owner Operators job openings in Kentucky as of August 2026, with employment types broken down into 90% Full Time, 8% Part Time, and 2% Contract. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution, with an average salary of $198,524 per year, or $95.4 per hour.

Chicago Intermodal Owner Operators

Truck Insure

On-site

$118 - $141/hr

Other

Posted 4 days ago


Job description

Contract | Owner Operator | Current as of Aug 24, 2026

CW Freight is looking to add experienced Owner Operators for local and regional intermodal work out of our Chicago operation.

Description

Contract | Owner Operator | Current as of Aug 24, 2026

CW Freight is looking to add experienced Owner Operators for local and regional intermodal work out of our Chicago operation.

CW Freight

Agency of Wall Street Intermodal, LLC

USDOTMust sign in | MC 762864

  • Hands-on experience with electronic equipment and software
Pay and Benefits
  • 70% of linehaul + accessorials
  • 100% FSC
  • 100% tolls
  • Typical 5-day regional settlement: $2,600–$3,100/week
  • Weekly direct deposit
  • Chassis splits paid when applicable - Rail detention paid when billable after free time
#J-18808-Ljbffr