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Leasing On Owner Operators Jobs in Chicago, IL (NOW HIRING)

CHASE LOGISTICS LLC

OTR CDL-A Owner Operator

Chicago, IL · On-site

$3.5K - $6.0K/wk

... A Owner Operators to haul dry van freight for major carriers, including FedEx, USPS, UPS, and ... Must own or lease your own tractor * Safe driving record * Ability to meet all DOT requirements

CEVA

CDL A OTR Team Owner Operators

West Chicago, IL

$480K/yr

CEVA Logistics is Contracting CDL A OTR Team Owner Operators and Solos Willing to Match Gross up to $480,000 per year Revenue and Earnings: * Team Tractor Owner Operators have the potential to gross ...

CEVA

CDL A OTR Team Owner Operators

Darien, IL

$480K/yr

CEVA Logistics is Contracting CDL A OTR Team Owner Operators and Solos Willing to Match Gross up to $480,000 per year Revenue and Earnings: * Team Tractor Owner Operators have the potential to gross ...

CEVA

CDL A OTR Team Owner Operators

Saint John, IN

$480K/yr

CEVA Logistics is Contracting CDL A OTR Team Owner Operators and Solos Willing to Match Gross up to $480,000 per year Revenue and Earnings: * Team Tractor Owner Operators have the potential to gross ...

CEVA

CDL A OTR Team Owner Operators

Schiller Park, IL

$480K/yr

CEVA Logistics is Contracting CDL A OTR Team Owner Operators and Solos Willing to Match Gross up to $480,000 per year Revenue and Earnings: * Team Tractor Owner Operators have the potential to gross ...

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Leasing On Owner Operators information

What are the key skills and qualifications needed to thrive as a leasing on owner operator?

To thrive as a Leasing On Owner Operator, you need a valid commercial driver's license (CDL), a clean driving record, and a solid understanding of federal transportation regulations. Familiarity with electronic logging devices (ELDs), freight management systems, and vehicle maintenance is typically required. Strong time management, self-motivation, and communication skills help you build relationships with carriers and manage the demands of independent trucking. These competencies ensure safe, efficient, and profitable operations while maintaining compliance and customer satisfaction.

What are some common challenges leasing on owner operators face during the onboarding process with a new carrier?

Leasing On Owner Operators often encounter challenges such as understanding the carrier's specific compliance requirements, adapting to new dispatch systems, and ensuring all necessary documentation (like insurance and permits) is in place. Additionally, adjusting to the carrier's operational expectations and learning their payment structure can take time. Open communication with the carrier's support team and other leased operators can help ease the transition and set expectations for a successful partnership.

What is the difference between Leasing On Owner Operators vs Truck Drivers?

AspectLeasing On Owner OperatorsTruck Drivers
CredentialsCommercial Driver's License (CDL), experience in freight haulingCDL, basic driving experience
Work EnvironmentOperate own trucks under lease agreements, manage own schedulesDrive company-owned trucks, follow employer schedules
Employer & Industry UsageLeasing companies, owner-operator programs in freight industryMotor carriers, logistics companies

Leasing On Owner Operators typically own or lease their trucks and operate independently under lease agreements, managing their schedules and expenses. Truck Drivers usually work for a company, driving company-owned trucks and following employer directives. Both roles require a CDL and involve freight hauling, but leasing on offers more independence and potential profit, while truck driving provides more stability and employer support.

How to become a leasing on owner operator?

To become a leasing on owner operator, you typically need to have a valid commercial driver's license (CDL), own or lease a qualifying truck, and meet the carrier's insurance and safety requirements. Gaining experience as a company driver can also improve your chances, and understanding lease agreements and industry regulations is essential for success in this role.

What are popular job titles related to Leasing On Owner Operators jobs in Chicago, IL?

For Leasing On Owner Operators jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Leasing On Owner Operators jobs in Chicago, IL look for?

The top searched job categories for Leasing On Owner Operators jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Leasing On Owner Operators jobs?

Cities near Chicago, IL with the most Leasing On Owner Operators job openings:

Leasing On Owner Operators jobs near you
Infographic showing various Leasing On Owner Operators job openings in Chicago, IL as of August 2026, with employment types broken down into 85% Full Time, 12% Part Time, and 3% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution.

CDL A OWNER OPERATORS NEEDED! Home on WEEKENDS! 75% Linehaul

Drive Time Transports

Chicago, IL

$3.0K - $4.0K/wk

Full-time

Re-posted 29 days ago

Job description

CDL-A OWNER OPERATORS! HOME EVERY WEEKEND (Can stay out longer if you would like)

TAKE HOME WEEKLY $3000 - $4000 (75% of the linehaul and 100% of the fuel surcharge)

$2000 SIGN ON BONUS!

EXPERIENCE REQUIREMENTS:

  • Must have 2 years of verifiable CDL experience
  • 1 year must be operating the same type of CMV on all equipment except van

Urine only drug test


IRP Plates: $200.00 deposit required, along with title and copy of paid 2290 per truck. Weekly debits until plate is paid in full. Plate cost varies based on request timing. Signed Plate program agreement required. AL/Cargo Insurance: Provided for all trucks at no cost NTL and OCAC Insurance: OCAC: $30.00/week OCAC is required but may be purchased elsewhere If providing own, must provide certificate naming us as additional insured Only available to Owner Operators Fleet Driver would need proof of coverage from the Fleet Owner NTL: $9.00/week NTL is required but may be purchased elsewhere If providing own, must provide certificate naming us as additional insured PD Insurance: Available at discounted rate based on truck value If providing own, must provide certificate naming us as additional insured Maximum coverage up to $250,000 Passenger Insurance: $4.50/week All passengers must be 18 years or older. Copy or driver's license or ID card required for passenger authorization letter from insurance Must complete Passenger Authorization application on Tenstreet 24-hour notice is needed to insurance time to process Escrow: Trucks: $100.00/week deducted until $1,500 cap. Optional maintenance escrow available for owner operators upon request. Drug Screen: Charged to fleet owner or owner-operator's first settlement Cost debited if leasing process not pursued to agents' or fleet owner's settlement Average cost is $42.00 to $61.00 depending on the clinic location IFTA: Debited every 3 months Calculation based on corporate MPG EFS/Fuel: Based on % of load Owner/Operator Benefits: Average 2,000 - 2,500 miles per week Company freight when available Non-forced dispatch Fuel discounts Access to Fuel Book app Weekly settlements Auto Liability Insurance included in our truck program Plate Program Trailer rental with maintenance available


Click apply now to get scheduled for orientation.
DriveTime Transports stands for safe, secure, and reliable transportation services delivered by a network of independent freight agents, company drivers,
leased owner-operators, and other third-party capacity providers. We empower these entrepreneurs to offer customized shipping solutions.
DriveTime Transports is a worldwide asset-light provider of integrated transportation management solutions delivering safe, specialized transportation services
to a broad range of customers utilizing a network of agents, third-party capacity owners, and employees.
At DriveTime Transports we are proud to be an Equal Opportunity and Affirmative Action employer and considers qualified applicants without regard to race,
color, creed, religion, ancestry, national origin, sex, sexual orientation, gender identity, age, disability, veteran status, or any other protected factor under federal, state, or local law.

Employment Type: FULL_TIME

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