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

DSL Express

Class A Owner - Operator OTR Driver

Alsip, IL · On-site

$312K - $460K/yr

We are offering the first 10 owners a ONE TIME DEAL. 92% linehaul (92/8) with only $200 deduction ... Solo Owner Operator Gross Pay: * Expect OTR avg Gross 5K to 8K+ per week during this post covid ...

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Showing results 1-20

All JobsOwner Operator Linehaul JobsOwner Operator Linehaul Jobs in Chicago, IL

Owner Operator Linehaul information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do owner operator linehaul jobs pay per week?

As of Sep 4, 2026, the average weekly pay for owner operator linehaul 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 is an owner operator linehaul?

Owner Operator Linehaul jobs involve professional truck drivers who own and operate their own vehicles, transporting freight over long distances between terminals or distribution centers. These operators are typically contracted by freight companies to move goods along set routes, often between cities or across states. As business owners, they are responsible for managing their schedules, maintaining their trucks, and handling business expenses. Linehaul routes generally involve less frequent stops and longer hauls compared to local delivery jobs. This role offers independence and the potential for higher earnings, but also requires strong business management skills.

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

To thrive as an Owner Operator Linehaul, you need a valid commercial driver’s license (CDL), strong knowledge of DOT regulations, and experience with long-haul trucking. Familiarity with GPS navigation, electronic logging devices (ELDs), and basic vehicle maintenance tools is essential. Excellent time management, self-motivation, and communication skills help you effectively manage routes and maintain customer relationships. These competencies are crucial for ensuring safe, efficient deliveries and the profitability of your independent trucking business.

What are some common challenges faced by owner operator linehaul drivers, and how can they be managed?

Owner Operator Linehaul drivers often encounter challenges such as managing long-haul schedules, maintaining their own vehicles, and navigating complex logistics networks. Balancing time on the road with personal life can be demanding, and unexpected maintenance issues may impact delivery timelines. Successful drivers typically stay organized with route planning, invest in regular vehicle upkeep, and maintain strong communication with dispatchers and shippers to ensure smooth operations.

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

AspectOwner Operator LinehaulTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving skills
Work EnvironmentOperate own truck on long-haul routesDrive company trucks, often shorter routes
EmployerSelf-employed or lease ownerEmployers or fleet companies
Work FocusManaging own business, route planningFollowing company routes and policies

Owner Operator Linehaul drivers typically own and operate their trucks, managing their routes and business aspects, while Truck Drivers usually work for a company, following established routes. Both roles require a CDL, but Owner Operators handle more business responsibilities, making them more independent.

What are popular job titles related to Owner Operator Linehaul jobs in Chicago, IL?

For Owner Operator Linehaul jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Owner Operator Linehaul jobs in Chicago, IL look for?

The top searched job categories for Owner Operator Linehaul jobs in Chicago, IL are:

Owner Operator Linehaul jobs near you
Infographic showing various Owner Operator Linehaul job openings in Chicago, IL as of August 2026, with employment types broken down into 47% Full Time, 51% Part Time, 1% Contract, and 1% Nights. 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.

Chicago Intermodal Owner Operators

Truck Insure

Chicago, IL • On-site

$118 - $141/hr

Other

Posted 3 days ago

New

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
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