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

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Weekend Owner Operator information

See Chicago, IL salary details

$663

$4.5K

$7.9K

How much do weekend owner operator jobs pay per week?

As of Aug 7, 2026, the average weekly pay for weekend 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 are common challenges faced by weekend owner operators, and how can they be managed?

Weekend Owner Operators often encounter challenges such as tight delivery schedules, limited access to support services during off-hours, and balancing personal time with work commitments. To manage these effectively, it's important to plan routes in advance, maintain strong communication with dispatchers and clients, and ensure your vehicle is well-maintained to minimize unexpected issues. Building a reliable network of contacts and staying organized can also help mitigate stress and ensure smooth operations during weekend shifts.

What skills and qualifications are needed to thrive as a weekend owner operator?

To thrive as a Weekend Owner Operator, you need a valid commercial driver's license (CDL), a clean driving record, and strong knowledge of transportation regulations. Familiarity with logistics software, GPS navigation systems, and electronic logging devices (ELDs) is typically required. Strong time management, self-motivation, and communication skills help you manage deliveries and coordinate with dispatchers or clients. These competencies ensure on-time deliveries, compliance with safety standards, and the successful management of your independent business.

What is a weekend owner operator?

A Weekend Owner Operator is a self-employed truck driver who owns or leases their own commercial vehicle and typically works on weekends transporting goods. They contract with companies or brokers to haul freight, often having flexibility to choose their loads and work schedule. This role appeals to drivers seeking supplemental income or a work-life balance that accommodates weekday commitments. Weekend Owner Operators are responsible for managing their business expenses, maintenance, and compliance with transportation regulations.

What is the difference between Weekend Owner Operator vs Part-Time Delivery Driver?

AspectWeekend Owner OperatorPart-Time Delivery Driver
CredentialsCommercial driver's license (CDL) often required, vehicle insuranceValid driver's license, sometimes a background check
Work EnvironmentOwns and operates their vehicle, flexible schedule, independentWorks for a company, scheduled shifts, company vehicle often provided
Employer & IndustryIndependent contractor in freight or logisticsEmployee or contractor in delivery services

Weekend Owner Operators typically own their vehicle and operate independently, often in freight or logistics, with more flexibility. Part-Time Delivery Drivers usually work for a company, with scheduled shifts and less operational responsibility. Both roles involve driving, but the ownership and independence level differ significantly.

What are the most commonly searched types of Owner Operator jobs in Chicago, IL? The most popular types of Owner Operator jobs in Chicago, IL are:
Weekend Owner Operator jobs near you

CDL- A Regional Owner Operator

Trimac Transportation

Chicago, IL • On-site

$3.5K - $5.5K/wk

Full-time

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

Job description

Overview

Trimac isn't just a transportation company; it's a powerhouse with a remarkable 75-year legacy safely delivering products that improve people’s lives across North America. We're not just moving goods; we're propelling lives forward by adapting to an ever-evolving landscape. Safety is our top priority, and we champion this through comprehensive safety training, state-of-the-art equipment, and cutting-edge technologies. Our drivers experience a world of opportunities, from transporting chemicals to handling dry or liquid bulk goods and specialized transportation services. 

We know it’s not just about the job; it's about your journey. We're passionate about your growth. We offer pathways to advancement, skills enhancement, and additional certifications or licenses because your success is our success. We’re proud of our diverse, vibrant, and supportive culture that cares about your well-being. If you’re ready for a challenge that comes with stability, growth, and a fulfilling work environment, start your journey with Trimac today.  

Contact our team of in-house Recruiters: 1-866-8-TRIMAC

Pay Details
  • Average weekly Gross $4500-$5500
  • Guaranteed $3500/wk* minimum
  • New $5,000 Sign-on-Bonus
  • Loaded Miles: $1.80 CPM, Empty Miles: $1.30 CPM
  • Fuel Surcharge
  • Weekly direct deposit
Schedule
  • Dispatched out 1-3 nights at a time
  • Weekly home time
  • Some weekend work required
  • Out and Back runs
  • Average weekly miles: 2000-2500
Who You Are

Are you a hard working driver with a great work ethic? We'd love to have you join our Team! Join us at Trimac and see the difference in working with a Company that's been in the industry since 1945!

Responsibilities
  • Safely delivering shipments to assigned customers.
  • Completion of all required paperwork, including getting required signatures on documents and bill of ladings
  • Maintaining and complying with all state and federal laws
  • Obeying DOT and FMCSA E-log requirements
  • Submitting all load documents in a timely manner
  • Upholding a professional attitude at all times
  • Keeping load appointments on time and as scheduled
Qualifications
  • Valid Class A Commercial Driver's License
  • Current Medical Certificate
  • Tanker and Hazmat endorsement required
  • TWIC required
  • Pass Trimac safety assessment
  • No pump or compressor needed for this position

Your Profile:


Past 7 years without:

  • Driving violation involving the consumption of illegal or intoxicating substances
  • A preventable rollover or fatality crash

Past 3 years without:

  • License suspensions involving drug and/or alcohol, or a record that would indicate a disregard for public safety
  • A major preventable accident
  • Two or more moving convictions
Additional Perks
  • Fuel card provided – Save more with business-to-business fuel discounts
  • All tolls covered
  • Discounts on tires and maintenance
Safety Commitments
  • We make safety a part of every decision
  • We make safety personal
  • We have the courage to intervene
Pay RangeUSD $3,500.00 - USD $5,500.00 /Wk.MarketChicago, IL

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