Delivery Driver Jobs in Winchester, IL — Start This Week

As of April 2026, there are 172 delivery driver openings in Winchester, IL. Local pay ranges from $500 to $8,925/year. Listings are updated daily — benefits start Day 1 for most positions.

Grubhub

Weekend Grubhub Delivery Professional

Winchester, IL

$2,420 - $4,180

Grubhub

Night Shift Grubhub Courier

Winchester, IL

$2,548 - $4,368

Uber

Flexible Ubereats Large Order Delivery Driver(Winchester)

Winchester, IL

$4,024 - $6,899

Shipt

Weekend Shift:Driver Opportunity-Winchester

Winchester, KY

$2,500 - $4,500

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Winchester, IL

$2,300 - $4,600

Grubhub

Grubhub Bicycle & Scooter Courier

Winchester, KY

$2,700 - $4,860

Lyft

Winchester-based Part-time Rideshare Driver Opening | Hiring

Winchester, ID

$500 - $1,500

Shipt

Evening & Night Shift Courier(Part-Time)@ Shipt-Winchester

Winchester, ID

$2,800 - $4,800

Uber

Flexible Ubereats Bicycle & Scooter Courier(Winchester)

Winchester, IL

$2,500 - $4,500

Uber

Winchester:Night Shift Rideshare Driver(Contractor,$3.2k-$5.5k/Month)

Winchester, NV

$3,200 - $5,500

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winchester, KY

$3,219 - $5,750

Uber

Rideshare Driver-Winchester,ID | Hiring

Winchester, ID

$3,000 - $5,000

Delivery Driver Jobs in Winchester — FAQ

How many delivery driver jobs are open in Winchester, IL?
There are currently 172+ 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 172+ 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

Other Driving Jobs in Winchester

12 open positions

Part-Time Driving Jobs in Winchester

12 open positions

Warehouse Jobs in Winchester

2 open positions

Grocery Jobs in Winchester

1 open positions

Weekend Driving Jobs in Winchester

1 open positions

Last updated: April 17, 2026