Driving Jobs in Winterset, IA — Now Hiring

As of April 2026, there are 30+ open driving positions in Winterset, IA. Current pay ranges from $896 to $8,500 per year. Most openings are in Delivery Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Grubhub Large Order Delivery Driver

Winterset, IA

$3,780 - $6,480

United Parcel Service (UPS)

UPS Package Delivery Driver(Logistics And Transportation)Vacancy in

Winterset, IA

$4,000 - $7,500

Midnight Logistics

(Winterset)Part-Time:Late Night Convenience & Grocery Courier

Winterset, IA

$2,800 - $4,800

Heavy Freight Logistics

Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,000 - $8,500

FreshDrop Logistics

Winterset Needs:Driver Opportunity(Part-Time)

Winterset, IA

$3,000 - $5,500

Urban Pedal Logistics

Start ASAP:Courier(Winterset)

Winterset, IA

$2,500 - $4,500

Suburban Delivery Network

Hiring in Winterset:Driver Opportunity(Part-Time)

Winterset, IA

$2,800 - $4,800

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Winterset, IA

$2,800 - $5,000

Grubhub

Night Shift Grubhub Courier

Winterset, IA

$3,080 - $5,280

Urban Pedal Logistics

Urgent Hire in Winterset:Independent Contractor Driver-Urban

Winterset, IA

$2,500 - $4,500

Auto Logistics Pros

Winterset Independent Contractor Driver-Auto Parts Courier

Winterset, IA

$2,800 - $4,800

Final Mile Delivery Co.

$3k-$5.5k/Month Independent Contractor Driver-Final Mile Parcel job in

Winterset, IA

$3,000 - $5,500

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 30+ open driving positions in Winterset, IA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Winterset?
Driving job pay in Winterset varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Winterset?
Yes. Many delivery driver, courier, and DSP positions in Winterset require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Winterset?
Driving jobs in Winterset offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Winterset?
Benefits vary by employer, but many driving positions in Winterset offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Winterset?
Your take-home pay as a driver in Winterset depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Winterset?
Yes, many driving positions in Winterset are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 30+ listings above and apply directly.

Last updated: April 26, 2026