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

Webb Hyundai Highland

Sales Lot Attendant

Highland, IN

$15/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Handle vehicle pick-ups, drop-offs, and dealer trades * Ensure vehicles are locked at closing and ...

Webb Hyundai Highland

Sales Lot Attendant

Highland, IN · On-site

$15/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Handle vehicle pick-ups, drop-offs, and dealer trades * Ensure vehicles are locked at closing and ...

Webb Hyundai Highland

Sales Lot Attendant

Highland, IN · On-site

$15/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Handle vehicle pick-ups, drop-offs, and dealer trades * Ensure vehicles are locked at closing and ...

Webb Hyundai Highland

Sales Lot Attendant

Highland, IN

$15/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Handle vehicle pick-ups, drop-offs, and dealer trades * Ensure vehicles are locked at closing and ...

Webb Hyundai Highland

Sales Lot Attendant

Highland, IN · On-site

$15/hr

About Us Webb Automotive is a family-owned and operated dealership group serving the Chicagoland ... Handle vehicle pick-ups, drop-offs, and dealer trades * Ensure vehicles are locked at closing and ...

Technipaq

Flexo Press Helper

Cary, IL · On-site

$20 - $22/hr

... set-ups OR 1+ year doing more complex car mechanics);Must be able to make and interpret ... Technipaq is family owned and operated serving the medical device and pharmaceutical packaging ...

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All JobsUps Owner Operator JobsUps Owner Operator Jobs in Chicago, IL

Ups Owner Operator information

See Chicago, IL salary details

$664

$4.5K

$7.9K

How much do ups owner operator jobs pay per week?

As of Aug 26, 2026, the average weekly pay for ups owner operator in Chicago, IL is $4,531.77, according to ZipRecruiter salary data. Most workers in this role earn between $2,478.85 and $6,740.38 per week, depending on experience, location, and employer.

What is a UPS Owner Operator?

A UPS Owner Operator is an independent contractor who owns and operates their own delivery vehicle while partnering with UPS to transport packages. Unlike company drivers, owner operators manage their own expenses, such as fuel, maintenance, and insurance. They have more control over their schedules and routes but must meet UPS’s delivery standards and contract requirements. This role can offer higher earning potential compared to company drivers, but it also comes with additional responsibilities and costs.

What are the typical daily responsibilities of a UPS Owner Operator?

UPS Owner Operators are responsible for safely transporting packages between distribution centers and customer locations while managing their own business operations. Typical duties include route planning, vehicle maintenance, handling shipping documentation, and ensuring timely deliveries in line with UPS standards. You’ll frequently communicate with dispatchers, customers, and warehouse staff to coordinate pickups and drop-offs. Adapting to changing delivery schedules and maintaining excellent customer service are also central to the role.

What are the key skills and qualifications needed to thrive as a UPS Owner Operator?

To thrive as a UPS Owner Operator, you need a valid commercial driver’s license (CDL), clean driving record, in-depth knowledge of logistics, and strong business management skills. Experience with fleet management software, route optimization tools, and compliance with Department of Transportation (DOT) regulations is highly valuable. Excellent customer service, time management, and problem-solving abilities help set top performers apart. These skills ensure safe, efficient deliveries and successful independent business operations within UPS's logistics network.

What are the most commonly searched types of Ups Owner Operator jobs in Chicago, IL?

The most popular types of Ups Owner Operator jobs in Chicago, IL are:

What are popular job titles related to Ups Owner Operator jobs in Chicago, IL?

For Ups Owner Operator jobs in Chicago, IL, the most frequently searched job titles are:

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The top searched job categories for Ups Owner Operator jobs in Chicago, IL are:

Ups Owner Operator jobs near you
Infographic showing various Ups Owner Operator job openings in Chicago, IL as of August 2026, with employment types broken down into 47% Full Time, 51% Part Time, 1% Contract, and 1% Nights. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $235,652 per year, or $113.3 per hour.

OTR CDL-A Owner Operator

CHASE LOGISTICS LLC

Chicago, IL • On-site

$3.5K - $6.0K/wk

Full-time

Re-posted 26 days ago

Job description

Join our team as an OTR CDL-A Owner Operator!

We're looking for safe, reliable, and professional Over-the-Road (OTR) CDL-A Owner Operators to haul dry van freight for major carriers, including FedEx, USPS, UPS, and Amazon.

What You'll Do

  • Haul dry van freight safely and efficiently
  • Run OTR routes with consistent freight opportunities
  • Work with a dedicated dispatch and ELD support team available 24/7

Freight Details

  • 80% Live Loads
  • 20% Drop & Hook
  • No-Touch Freight
  • No Forced Dispatch

Qualifications

  • Valid CDL-A license
  • Must own or lease your own tractor
  • Safe driving record
  • Ability to meet all DOT requirements
  • Strong commitment to safety and on-time deliveries

Why Drive With Us?

  • Consistent freight opportunities
  • No-touch freight
  • No forced dispatch
  • 24/7 dispatch and ELD support
  • Haul freight for established customers, including FedEx, USPS, UPS, and Amazon
  • Supportive team focused on keeping you moving

Apply today and partner with a team that values owner operators and keeps you on the road!