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Local Dedicated Owner Operator Jobs in Chicago, IL

ARL Network

CDL A Owner Operator

Chicago, IL

$2.5K - $3.5K/wk

Local intermodal: in and out of the rail yards every day -- no over-the-road, no weeks away from ... This is the typical weekly range for owner operators running a full schedule -- before fuel ...

ARL Network

CDL A Owner Operator

Joliet, IL

$2.5K - $3.5K/wk

Local intermodal: in and out of the rail yards every day -- no over-the-road, no weeks away from ... This is the typical weekly range for owner operators running a full schedule -- before fuel ...

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Showing results 21-40

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

Local Dedicated Owner Operator information

See Chicago, IL salary details

$1.2K

$4.6K

$7.7K

How much do local dedicated owner operator jobs pay per week?

As of Aug 22, 2026, the average weekly pay for local dedicated owner operator in Chicago, IL is $4,576.90, according to ZipRecruiter salary data. Most workers in this role earn between $1,334.62 and $7,459.62 per week, depending on experience, location, and employer.

What is a local dedicated owner operator?

A Local Dedicated Owner Operator is a self-employed truck driver who owns and operates their own commercial vehicle, and contracts with a specific company to transport goods within a designated local area. Unlike over-the-road drivers, local dedicated operators typically work regular routes and are home daily or nightly. They benefit from consistent schedules and steady work, but are also responsible for their truck’s maintenance, insurance, and other business expenses. This role combines the independence of being an owner-operator with the stability of dedicated routes.

What are the key skills and qualifications needed to thrive as a local dedicated owner operator?

To thrive as a Local Dedicated Owner Operator, you need a valid commercial driver’s license (CDL), a clean driving record, business acumen, and experience with local freight routes. Familiarity with electronic logging devices (ELDs), route planning software, and basic truck maintenance tools is typically required. Strong organizational skills, self-motivation, and excellent customer service abilities set top performers apart. These skills and qualities are crucial for ensuring timely deliveries, operational efficiency, and sustained business success in a competitive transportation market.

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

Local Dedicated Owner Operators often face challenges such as maintaining consistent routes, managing vehicle maintenance, and balancing work-life commitments due to tight delivery schedules. Building strong relationships with dispatchers and shippers can help secure regular loads and minimize downtime. Additionally, staying proactive with vehicle upkeep and leveraging route planning technology can reduce unexpected delays and expenses, while clear communication with clients and family can support work-life balance.

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

AspectLocal Dedicated Owner OperatorLocal Company Driver
CredentialsCommercial Driver's License (CDL), experience in hauling specific freightCDL, basic driving experience
Work EnvironmentOperate own truck, flexible schedules, independent workDrive company-owned trucks, structured schedules
Employer & Industry UsageFreight carriers, logistics companies, owner-operated fleetsCarriers, logistics firms, large transportation companies

In summary, Local Dedicated Owner Operators own and operate their trucks, offering flexibility and independence, while Local Company Drivers work for a company using their trucks with more structured schedules. Both roles require a CDL and are common in local freight hauling, but differ mainly in ownership and work setup.

What are the most commonly searched types of Dedicated Owner Operator jobs in Chicago, IL?

The most popular types of Dedicated Owner Operator jobs in Chicago, IL are:

Local Dedicated Owner Operator jobs near you
Infographic showing various Local Dedicated Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 69% Full Time, 26% Part Time, and 4% Contract. Highlights an 95% Physical, 2% Hybrid, and 3% Remote job distribution, with an average salary of $237,999 per year, or $114.4 per hour.

Cargo Van Owner Operator - Nationwide Loads

Double Leap LLC

Chicago, IL • On-site

Other

Re-posted 12 days ago

Job description

Owner-Operators (Sprinter Vans & Cargo Vans) – Nationwide

Double Leap LLC is seeking reliable owner-operators with Sprinter Vans or Cargo Vans for OTR, regional, and local opportunities across the United States and Canada.

What We Offer:

  • No forced dispatch.
  • Weekly pay.
  • Consistent freight opportunities.
  • Flexible schedule.
  • OTR, regional & local loads.
  • 24/7 dispatch support.

Requirements:

  • Sprinter Van or Cargo Van.
  • Valid driver's license.
  • Commercial insurance.
  • Clean motor vehicle record (MVR).
  • Professional and dependable attitude.

Take control of your schedule and grow your business with a trusted logistics partner.

Nina (HR) 469-242-2912 nina@doubleleapllc.com

Double Leap logo

About Double Leap

Sourced by ZipRecruiter

Double Leap is a North American logistics and transportation company that is ever-growing. We believe our value is in our team and our client relationships. Double Leap exists to provide excellent transportation services to all freight to our clients. We pride ourselves on delivering time-sensitive and customized solutions to every clients. We take the responsibility to operate safely, as well as look out for new innovation and improvements to look forward for better and smarter logistics.

Industry

Transportation and warehousing

Company size

11 - 50 Employees

Headquarters location

Euless, TX, US

Year founded

2019

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