UPS CDL Driver Jobs in Winchester, IL — Hiring Now

As of October 2026, there are 24 UPS cdl driver openings in Winchester, IL. Local pay ranges from $20 to $54/hr. Listings are updated daily — benefits start Day 1 for most positions.

UPS

UPS Seasonal Driver — No CDL Required, Immediate Start

Winchester, IL

$22 - $29

UPS

UPS CDL Apprentice Driver — Earn Your CDL While You Work

Winchester, KY

$24 - $42

UPS

UPS CDL Apprentice Driver — Earn Your CDL While You Work

Winchester, ID

$20 - $35

UPS

CDL Apprentice Driver—Earn Your CDL While You Work(Package Logistics

Winchester, ID

$24 - $42

UPS

Winchester Feeder Driver—CDL Class A Tractor-trailer

Winchester, NV

$35 - $50

UPS

UPS seeks Seasonal Driver—No CDL Required,Immediate Start in

Winchester, IL

$21 - $28

UPS

Feeder Driver—CDL Class A Tractor-trailer Career Needed-Winchester

Winchester, ID

$35 - $50

UPS

Join Team in Winchester:Seasonal Driver—No CDL Required,Immediate

Winchester, NV

$21 - $28

UPS

UPS Needs Seasonal Driver—No CDL Required,Immediate Start in

Winchester, ID

$21 - $28

UPS

UPS CDL Apprentice Driver — Earn Your CDL While You Work

Winchester, IL

$21 - $36

UPS

UPS Feeder Driver — CDL Class A Tractor-Trailer Career

Winchester, IL

$32 - $46

UPS

UPS Seasonal Driver — No CDL Required, Immediate Start

Winchester, ID

$21 - $28

UPS CDL Driver Jobs in Winchester — FAQ

How many UPS cdl driver jobs are open in Winchester, IL?
There are currently 24+ UPS cdl driver positions in Winchester, IL. New cdl driver roles are added regularly — check this page for the latest openings.
How much do UPS cdl driver jobs pay in Winchester?
UPS cdl driver pay in Winchester varies by specific role and shift. Most positions include shift differentials for nights and weekends, plus benefits starting Day 1. Browse the listings above to see pay details for each opening.
Does UPS hire for cdl driver positions with no experience in Winchester?
Many UPS cdl driver positions in Winchester require no prior experience. UPS provides paid training for new hires. Check individual listings for specific requirements.
How do I apply for UPS cdl driver jobs in Winchester?
Browse the 24+ cdl driver listings above, click on any position for full details including pay and shift times, then follow the application link. Most UPS positions have a 15–30 minute online application.

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Other UPS Jobs in Winchester

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172 open positions

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UPS Other UPS Jobs in Winchester

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UPS Sortation Center Jobs in Winchester

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Last updated: October 26, 2026