Delivery Driver Jobs in Winterset, IA — Start This Week

As of April 2026, there are 43 delivery driver openings in Winterset, IA. Local pay ranges from $500 to $9,180/year. Listings are updated daily — benefits start Day 1 for most positions.

Grubhub

Early Morning Grubhub Driver

Winterset, IA

$2,420 - $4,180

Last Mile Logistics Network

Independent Contractor Driver - Last-Mile Logistics

Winterset, IA

$2,576 - $4,600

Uber

Night Shift Ubereats Courier|Flexible|Winterset

Winterset, IA

$2,548 - $4,368

Grubhub

Grubhub Shop and Pay Driver

Winterset, IA

$2,576 - $4,416

Lyft

$2.8k-$5k/Month Event Rideshare Driver job in Winterset | Hiring

Winterset, IA

$2,800 - $5,000

Uber

Rideshare Driver Needed-Winterset Area | Hiring

Winterset, IA

$3,000 - $5,000

Shipt

Winterset Job:Evening & Night Shift Courier(No Exp Req*)

Winterset, IA

$2,800 - $4,800

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winterset, IA

$896 - $2,016

Uber

Winterset Part-time Ubereats Driver(lunch Rush)(Gig)

Winterset, IA

$736 - $1,656

Grubhub

Grubhub Bicycle & Scooter Courier

Winterset, IA

$2,700 - $4,860

Uber

Winterset Connect Package Delivery Driver(Gig)

Winterset, IA

$3,000 - $5,500

Grubhub

Suburban Route Grubhub Driver

Winterset, IA

$2,208 - $3,864

Delivery Driver Jobs in Winterset — FAQ

How many delivery driver jobs are open in Winterset, IA?
There are currently 43+ delivery driver positions in Winterset, IA. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winterset?
Delivery Driver pay in Winterset 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 Winterset require experience?
Many delivery driver positions in Winterset 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 Winterset?
Browse the 43+ 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 Winterset

Other Driving Jobs in Winterset

3 open positions

Part-Time Driving Jobs in Winterset

2 open positions

Weekend Driving Jobs in Winterset

1 open positions

Warehouse Jobs in Winterset

1 open positions

Last updated: April 17, 2026