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Drop Hook Owner Operator Jobs in Chicago, IL (NOW HIRING)

Forward Air

CDL-A Owner Operator Driver

Elwood, IL · On-site

$4.1K - $5.2K/wk

MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to $250,000 gross per year* Why Drive for Forward Air? At Forward Air, Owner Operators aren't just drivers, they're ...

Forward Air

CDL-A Owner Operator Driver

Chicago, IL · On-site

$4.1K - $5.2K/wk

MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to $250,000 gross per year* Why Drive for Forward Air? At Forward Air, Owner Operators aren't just drivers, they're ...

ARL Network

CDL A Owner Operator

Chicago, IL

$2.5K - $3.5K/wk

Load types: live load, live unload, and drop-and-hook. * Specialty work: some containers are ... This is the typical weekly range for owner operators running a full schedule -- before fuel ...

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All JobsDrop Hook Owner Operator JobsDrop Hook Owner Operator Jobs in Chicago, IL

Drop Hook Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do drop hook owner operator jobs pay per week?

As of Sep 3, 2026, the average weekly pay for drop hook 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 is a drop hook owner operator?

A Drop Hook Owner Operator is a truck driver who owns and operates their own truck while primarily handling drop and hook freight. This means they pick up pre-loaded trailers and drop off empty ones, minimizing wait times for loading and unloading. These operators typically work with companies or freight brokers to transport goods efficiently. Since there’s little to no live loading, the job allows for quicker turnaround times and more miles driven.

What are the typical daily responsibilities of a drop hook owner operator?

As a Drop Hook Owner Operator, your main daily tasks usually include picking up pre-loaded trailers, transporting them to designated locations, and dropping them off for unloading, often with minimal wait times. You'll handle inspections of your truck and trailer to ensure safety compliance, manage delivery documentation, and coordinate with dispatchers or warehouse staff as needed. Unlike traditional trucking roles, you generally do not load or unload freight, allowing for quicker turnarounds and higher route efficiency. This position often offers flexibility, autonomy, and the opportunity to maximize driving hours, making it attractive to owner operators seeking a steady schedule and increased earning potential.

What are the key skills and qualifications needed to thrive as a drop hook owner operator?

To thrive as a Drop Hook Owner Operator, you need a valid commercial driver's license (CDL), a keen understanding of logistics operations, and experience in safe and efficient trailer exchanges. Familiarity with electronic logging devices (ELDs), GPS navigation, and basic truck maintenance tools is typically required. Excellent time management, communication skills, and a strong sense of independence are standout qualities in this role. These skills are vital for maximizing earnings, maintaining safety, and delivering shipments efficiently in a fast-paced transportation environment.

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

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

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

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

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

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

What cities near Chicago, IL are hiring for Drop Hook Owner Operator jobs?

Cities near Chicago, IL with the most Drop Hook Owner Operator job openings:

Drop Hook Owner Operator jobs near you
Infographic showing various Drop Hook Owner Operator 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.

CDL Class A Owner Operator Intermodal Driver Home Daily

Legacy Intermodal

Chicago, IL • On-site

$5.5K/wk

Full-time

This job post has expired today. Applications are no longer accepted.

Job description


Job Description:
CDL Class A Owner Operator Intermodal Driver Home Daily

Legacy Intermodal is hiring experienced Owner Operators for container freight in Chicago and Dallas . Enjoy dedicated freight, steady year-round work, and daily home time while maximizing your weekly earnings with reliable dispatch and consistent loads.

Pay & Benefits:


Owner Operators

  • Earn $5,500 Gross Weekly
  • $5,000 Sign-On Bonus
  • FREE License Plate (No payments until March 31, 2027. Limited supply.)
  • IFTA filing with fuel card
  • Home Daily
  • Local & Regional Routes (200 miles or less)
  • Dedicated Freight
  • Steady Container Work
  • Drop & Hook
  • No Nickel & Dime Deductions
  • Reliable Dispatch & Year-Round Freight

Driver Requirements:

  • Valid CDL-A License
  • Owner Operator with a qualifying truck
  • Clean driving record preferred
  • TWIC Card preferred (if applicable)
  • Professional, reliable, and safety-focused


Why Drive With Legacy Intermodal?


We provide consistent freight, dependable pay, and the support Owner Operators need to succeed. Our goal is to keep you moving with dedicated container loads and reliable home time.


  • Home Daily
  • Dedicated Freight
  • Consistent Weekly Revenue
  • Experienced Dispatch Team
  • Long-Term Driver Partnerships
  • Strong Driver Support
Apply or call now! limited spots available

Apply