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

Norbet Trucking

Owner Operator EC

East Chicago, IN · On-site

No Weekends Maintain accurate records and logs. Perform vehicle inspections and preventative ... Pay: 75% owner-operator pay 100% fuel surcharge Stop & detention pay Liability & truck insurance ...

Home Instead

Weekend Caregiver

Crystal Lake, IL · On-site

$20/hr

Weekends About Home Instead Home Instead is a family-owned business that provides non-medical care ... Each Home Instead franchise is independently owned and operated. To find a franchise near you ...

Home Instead

Weekend Caregiver

Oak Park, IL · On-site

$18.50/hr

Weekends About Home Instead Home Instead is a family-owned business that provides non-medical care ... Each Home Instead franchise is independently owned and operated. To find a franchise near you ...

Right at Home

Weekend Caregiver

Merrillville, IN · On-site

$15 - $17/hr

Available shifts include days, evenings, nights, weekends, overnights, and live-ins. Opportunities ... This franchise is independently owned and operated by a franchisee. Your application will go ...

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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 Jul 15, 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 company in Texas is paying truckers $14000 a week?

Some trucking companies or owner-operators may report earning up to $14,000 weekly, especially with high-mileage loads, efficient routes, and proper equipment. However, such earnings are typically associated with experienced drivers working long hours or specialized freight, and actual pay varies based on factors like load type, experience, and market conditions.

What are some common challenges faced by Weekend Owner Operators, and how can they be managed effectively?

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 are the key skills and qualifications needed to thrive as a Weekend Owner Operator, and why are they important?

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.

Why do most people quit trucking?

Many truck drivers quit trucking due to long hours, time away from family, and challenging working conditions. The job often involves irregular schedules, physical and mental fatigue, and limited job stability, which can lead to burnout and high turnover rates.

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.

Which owner-operator pays the most?

The highest-paying owner-operator positions typically offer premium rates for specialized freight, long-haul routes, or dedicated contracts with large carriers. Factors such as experience, equipment, and negotiation skills also influence earnings, with some owner-operators earning over $200,000 annually. However, pay varies widely based on market conditions and individual arrangements.

What side hustle can I do with my truck?

Weekend owner operators can use their trucks for side hustles such as local delivery services, moving assistance, or hauling equipment, depending on truck size and licensing. These opportunities often require additional certifications like a commercial driver's license (CDL) and adherence to safety regulations.
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
Owner Operator EC

Owner Operator EC

Norbet Trucking

East Chicago, IN • On-site

Full-time

Re-posted yesterday

Job description

Hiring an experienced CDL-A Owner Operatorssteady loads, competitive rates, and a company you can rely on!

Responsible for driving your own tractor-trailer in compliance with applicable federal, state and local laws and regulations as well as company policies and procedures for transporting various materials in a safe and timely manner to regional or local customers.

Responsibilities:

Responsible for proper loading and securing freight to prevent movement and allow safe transport.
Assist in loading and unloading as required.
Layover is possible for 1 or 2 nights during the week. No Weekends
Maintain accurate records and logs.
Perform vehicle inspections and preventative maintenance before, during and after trips.
Works with dispatch for delivery assignments and road service throughout the day.
Reads bill of lading to determine assignment schedule.
If necessary, report all incidents and accidents accurately and timely within the scope of the company and DOT required processes.

    Experience:

    Experience hauling steel a plus
    Minimum three year's operating flatbed.
    Driving record must be three years traffic accident and violation free.

      Pay:

      75% owner-operator pay
      100% fuel surcharge
      Stop & detention pay
      Liability & truck insurance provided

      License:

      Commercial Driver's license A
      TWIC card beneficial