Join UPS in Chicago as a Weekend Delivery Driver—Weekdays Always Free

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Opportunity in Chicago

Snapshot

  • Benefits: A competitive compensation package is offered.
  • Position: Weekend Delivery Driver — Weekdays Always Free (Flexible/Contract, Chicago)
  • Hiring Organization: UPS
  • Apply your your professional skills skills at our Chicago location.
  • Join our Chicago team for this flexible role.
  • Salary: $23-$30/Hour (approx. $31.7k/Year)
  • Worksite: Chicago, IL
  • This Chicago-based role is an excellent opportunity for professionals skilled in relevant skills.
  • Our UPS team in Chicago, IL is growing.
  • Benefit from working in Chicago, a key hub for the Package Logistics And Last-mile Delivery industry.


About UPS & Our Culture

Monday through Friday belongs to you. Saturday and Sunday belong to UPS — and we pay exceptionally well for those two days. Our Weekend Delivery Driver program is one of the most strategically designed weekend driver jobs in the logistics industry, built specifically for professionals, parents, and students who need their weekday schedule completely untouched. As a UPS Weekend Delivery Driver, you operate a company-provided package car across residential routes on Saturday and Sunday, earning Teamsters union wages plus a weekend differential that makes two days of driving financially comparable to what most people earn working five. If you have been searching for weekend driver jobs near me that pay real money without touching your weekday life, this is the role.

What Our Team Says (Employee Reviews)

"I am a nurse Monday through Friday and a UPS Weekend Driver on Saturday and Sunday. The weekend differential on top of the package car wage rate means I earn very strong money for two days of work that are genuinely enjoyable. Driving routes in my own community, meeting customers, staying active — it does not feel like a second job most days. And the Teamsters benefits on top of my hospital plan have made my family's financial situation more secure than it has ever been." - Current Weekend Delivery Driver, Nashville, TN.

Role Overview & Responsibilities

As a UPS Weekend Delivery Driver, you operate a company-provided UPS package car across assigned residential and light commercial routes every Saturday and Sunday, delivering the weekend's elevated e-commerce volume while maintaining UPS's service standards on the two days of the week when customer delivery expectations are highest.

  • Weekend Route Execution: Complete 80 to 160 package stops across your assigned Saturday and Sunday routes, navigating residential neighborhoods using the UPS DIAD device and company GPS routing to maintain efficient stop sequencing throughout the day.
  • Elevated Weekend Volume Management: Handle the above-average residential package volume that accumulates through the week and peaks on Saturday, adapting your stop pacing and route prioritization to clear the full manifest within the delivery window.
  • Customer Doorstep Service: Deliver every package with the professionalism the UPS brand demands — proper placement, correct signature capture where required, and friendly but efficient customer interaction that earns the high satisfaction scores UPS monitors for every driver.

Benefits & Perks

UPS Weekend Delivery Drivers earn Teamsters union package car wages plus a weekend shift differential, with full medical, dental, and vision benefits, pension contributions, paid personal time, and weekly direct-deposit paychecks — all without sacrificing a single weekday hour. A company-provided package car means zero personal vehicle wear. This is the most schedule-friendly premium weekend driver job available in the delivery industry.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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