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

Right at Home

Weekend Caregiver

Merrillville, IN · On-site

$15 - $17/hr

  • Medical

  • Dental

  • Life

  • PTO

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 ...

HCAOA

Weekend Caregiver

Hinsdale, IL · On-site

$14 - $16/hr

  • Medical

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 ...

Right at Home

Weekend Caregiver

Merrillville, IN · On-site

$15 - $17/hr

  • Medical

  • Dental

This franchise is independently owned and operated by a franchisee. Your application will go directly to the franchisee, and all hiring decisions will be made by the management of this franchisee.

McDonald's

Crew Team Member

Homer Glen, IL · On-site

$15 - $19/hr

  • PTO

... 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.

McDonald's

Crew Team Member

South Holland, IL · On-site

$15 - $19/hr

  • PTO

... 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.

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Showing results 21-40

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 Aug 17, 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

CDL-A Owner Operator - Nationwide Dry Van

American Global Express LLC

Gary, IN

$5.0K - $8.0K/wk

Full-time

Medical

Posted 10 days ago

Job description

American Global Express (AG-XP) is a family-owned carrier based in the St. Louis, MO area partnering with CDL-A owner operators on dedicated dry van freight. U.S.-based dispatch, no overseas call centers — we know you by name.

PAY
  • Weekly gross $5,000–$8,000
  • 80% to the truck, paid every Friday by direct deposit
  • Fuel card accepted at Love's, TA and Pilot
  • Plates, IFTA and liability insurance available
FREIGHT & FREEDOM
  • Dedicated dry van with consistent lanes
  • Primary lanes: Midwest, Mid-Atlantic, East Coast, Southeast and Ohio Valley
  • 100% non-forced dispatch — you choose your loads
  • Run under our authority
HOME TIME
  • Home every weekend, and home whenever you request — freight planned around you
EQUIPMENT & SUPPORT
  • Large dry van trailer pool — pick up your trailer in the St. Louis area
  • PrePass and Motive ELD provided and shipped to you
  • Dedicated dispatcher, 24/7 support
  • Phone orientation — fast, simple onboarding
ABOUT AMERICAN GLOBAL EXPRESS

We are a family-owned carrier headquartered in the St. Louis, MO area, running dry van freight throughout the Midwest. This is where we are based and where most drivers come to pick up their trailer. Our dispatch team is U.S.-based — you will know the people planning your freight by name.

Call or text Keith at 314-278-8841, or apply at ag-xp.com.

Requirements
  • Valid Class A CDL
  • 24 months verifiable CDL-A experience (exceptions reviewed)
  • Own truck, ready to run
  • Clean driving record
  • Current DOT medical card
Benefits
  • Weekly gross $5,000–$8,000
  • 80% to the truck, paid every Friday by direct deposit
  • 100% non-forced dispatch
  • Home every weekend and home whenever requested
  • Plates & IFTA available
  • Liability insurance available
  • Fuel card — Love's, TA, Pilot
  • Large dry van trailer pool — pick up your trailer in the St. Louis area
  • PrePass & Motive ELD provided and shipped to you
  • Run under our authority
  • U.S.-based dispatch and dedicated dispatcher
  • Phone orientation — fast, simple onboarding
  • Family-owned carrier that knows you by name

CDL Class A · Haul: OTR · Freight: Dry Van · Home time: Home every weekend; home whenever requested