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Weekend Owner Driver Jobs in Chicago, IL (NOW HIRING)

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Weekend Owner Driver information

See Chicago, IL salary details

$384

$1.7K

$4.9K

How much do weekend owner driver jobs pay per week?

As of Aug 8, 2026, the average weekly pay for weekend owner driver in Chicago, IL is $1,725.50, according to ZipRecruiter salary data. Most workers in this role earn between $720.46 and $1,855.44 per week, depending on experience, location, and employer.

What is a weekend owner driver?

A Weekend Owner Driver job involves using your own vehicle to complete delivery or transportation tasks on weekends. You are responsible for picking up and delivering goods, parcels, or passengers, depending on the company or service. This role offers flexibility, allowing you to choose your working hours while earning extra income. You must maintain your vehicle, have the necessary licenses and insurance, and meet the company's requirements. It’s ideal for those looking for part-time or supplemental income opportunities.

What are the key skills and qualifications needed to thrive as a weekend owner driver?

To thrive as a Weekend Owner Driver, you need a valid driver’s license, a reliable and insured vehicle, strong navigation skills, and good physical stamina. Familiarity with GPS and route optimization apps, as well as experience with electronic proof-of-delivery systems, are often required. Excellent time management, customer service, and problem-solving abilities help you stand out in this position. These skills are critical to ensure timely, efficient deliveries and build trust with clients while managing your schedule independently.

What are the typical challenges weekend owner drivers face on the job?

Weekend Owner Drivers often face challenges such as managing tight delivery schedules, navigating traffic, and handling last-minute changes or requests from clients. Since this role usually involves working independently, you’ll need to stay organized and proactive in resolving any issues that arise during your route. Additionally, balancing the physical demands, such as lifting packages and frequent driving, with providing excellent customer service can be demanding. However, many drivers find the independence and flexible weekend work schedule rewarding, especially when they develop efficient routines and relationships with regular customers.

What are the most commonly searched types of Owner Driver jobs in Chicago, IL? The most popular types of Owner Driver jobs in Chicago, IL are:
What are popular job titles related to Weekend Owner Driver jobs in Chicago, IL? For Weekend Owner Driver jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Weekend Owner Driver jobs in Chicago, IL look for? The top searched job categories for Weekend Owner Driver jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Weekend Owner Driver jobs? Cities near Chicago, IL with the most Weekend Owner Driver job openings:
Weekend Owner Driver jobs near you
Infographic showing various Weekend Owner Driver job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 29% Part Time, and 3% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $89,726 per year, or $43.1 per hour.

CDL-A Dedicated Driver | Home Every Weekend | Salary Pay

Drive Time Transports

Chicago, IL • On-site

$1.5K/wk

Full-time

Re-posted 27 days ago

Job description

CDL-A Dedicated | Salary Pay | Home Weekly

  • Avg weekly: $1,500

  • Salary position - paid weekly

  • Home every weekend (Sun-Fri)

  • No touch freight

  • Dry van

  • Steady lanes

States Run:
IA, IL, IN, MO, WI, KY, TN, OH, MI

Requirements:

  • CDL-A

  • 6 months experience

  • Some night driving required

  • 90 days unemployment

  • Accident reports required (last 5 years)

  • Pre-employment drug test is hair and urine

Additional requirements:
MINIMUM 6 MONTHS CDL-A TRACTOR TRAILER EXPERIENCE - MUST BE VERIFIABLE
No more than 2 MV's in the last 2 years. No serious traffic violations in the last 12 months.
No more than 1 on-road or DOT preventable loss in the last 2 years. No major preventable accidents in the last 5 years
No DUI/DWI within the past 10 years if the offense occurred while they held a CDL-A or Commercial Learners Permit. No DUI/DWI within the last 5 years if the offense occurred prior to getting a CDL-A
NO SAP DRIVERS

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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