Delivery Driver Jobs in Winchester, IL — Apply Today

As of May 2026, there are 156 delivery driver openings in Winchester, IL. Local pay ranges from $14 to $155,250/year. Listings are updated daily — benefits start Day 1 for most positions.

United Parcel Service (UPS)

IL Career:UPS Package Delivery Driver in Winchester | Hiring

Winchester, IL

$4,000 - $7,500

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional

Winchester, NV

$3,500 - $6,000

DoorDash

Delivery Driver-Food Delivery Part Time Evenings(Contract)-Winchester

Winchester, KY

$15 - $22

Amazon Flex

Immediate Opening in Winchester for a Holiday Peak Delivery Driver

Winchester, KY

$3,960 - $6,600

FedEx Ground

Work in Winchester:Delivery Driver-Package Handler | Hiring

Winchester, ID

$21 - $26

On-Demand Tasks Network

Winchester Job:Independent Contractor Driver-On-demand Errands

Winchester, KY

$2,000 - $4,000

Secure Document Couriers

Winchester Independent Contractor Driver-Night Shift Legal/document

Winchester, ID

$2,800 - $5,000

Postmates

Recruiting:Same-day Delivery Driver in Winchester,NV | Hiring

Winchester, NV

$2,944 - $4,968

GoPuff

Apply Now:Convenience Store Delivery Driver in Winchester | Hiring

Winchester, KY

$2,548 - $4,095

Domino's Pizza

Now Hiring:Delivery Driver-Pizza Delivery Tips Plus Wages in

Winchester, IL

$14 - $20

Shipt

Shipt seeks Pharmacy Delivery Driver in Winchester | Hiring

Winchester, NV

$2,728 - $4,576

Heavy Freight Logistics

Winchester-based Independent Contractor Driver-Cargo Van / Box Truck

Winchester, NV

$5,000 - $8,500

Delivery Driver Jobs in Winchester — FAQ

How many delivery driver jobs are open in Winchester, IL?
There are currently 156+ delivery driver positions in Winchester, IL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winchester?
Delivery Driver pay in Winchester varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winchester require experience?
Many delivery driver positions in Winchester welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winchester?
Browse the 156+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Other Driving Jobs in Winchester

Cdl Driver Jobs in Winchester

34 open positions

Other Driving Jobs in Winchester

5 open positions

Yard Jockey Jobs in Winchester

4 open positions

Overnight Driving Jobs in Winchester

1 open positions

Last updated: May 14, 2026