ZipRecruiter

Log In

1

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

HCAOA

Weekend Caregiver

Hinsdale, IL · On-site

$14 - $16/hr

Member businesses are independently owned and operated. Your application will go directly to the member business, and all hiring decisions will be made by the management of that business. All ...

HCAOA

Weekend Caregiver

Hinsdale, IL · On-site

$14 - $16/hr

Member businesses are independently owned and operated. Your application will go directly to the member business, and all hiring decisions will be made by the management of that business. All ...

HCAOA

Weekend Caregiver

Hinsdale, IL · On-site

$14 - $16/hr

Member businesses are independently owned and operated. Your application will go directly to the member business, and all hiring decisions will be made by the management of that business. All ...

McDonald's

Crew Team Member

Homer Glen, IL · On-site

$15 - $19/hr

... Owner/Operator. Crew Person - You don't want to work just anyplace, and you don't want to work just anytime. Maybe it's breakfast. Maybe it's lunch. Maybe it's late nights. Maybe it's weekends.

previous page

Showing results 41-60

All JobsOwner Operator JobsWeekend Owner Operator JobsWeekend Owner Operator Jobs in Chicago, IL

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 Sep 2, 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 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 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 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 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

Local CDL A Owner Operator Truck Drivers

Maersk Logistics & Services USA

Skokie, IL • On-site

$3.0K - $5.0K/wk

Full-time

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

Job description


Job Description:

Local CDL A Subhaulers W/ Own Authority


TIRED OF BROKERS PLAYING GAMES WITH RATES? If you have your own authority and at least 1 year active we want YOU. We built our pay model using real data from the American Transportation Research Institute (ATRI). That means transparent, industry-backed rates not made-up numbers.

TERMINAL IS LOCATED IN ELWOOD WHAT YOU GET:

  • Home Nightly
  • Tiered Rate Per Mile with GUARANTEED minimums
  • Fuel surcharge paid weekly
  • Pay: $3,000.00 - $5,000.00 per week
  • Detention after 2 hours
  • Hazmat / overweight / accessorial pay
  • Empty miles paid SAME as loaded
  • Bobtail paid at 80% of loaded rate
  • Weekly settlements

WEEKEND AVAILABILITY IS A PLUS****

No surprises. No rate switching. No runaround.

Wage Range: - per week

General Description of Benefits: 1099 Position

Requirements:

  • Your own authority established for at least 1 year
  • Active MC/DOT number
  • Insurance with us listed as additional insured
  • Occupational Accident Insurance and/or Workers Compensation
  • Public liability coverage (bodily injury, property damage, environmental restoration)
  • Cargo insurance
  • Non-Owned Trailer Physical Damage coverage
  • EIN documentation (Corporation documents)
  • Proof of random drug pool enrollment
  • Truck registration

Apply