Driving Jobs in Oskaloosa, IA — See Openings

As of September 2026, there are 20+ open driving positions in Oskaloosa, IA. Current pay ranges from $1,380 to $8,625 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Oskaloosa, IA

$3,850 - $6,600

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Oskaloosa, IA

$2,500 - $4,500

On-Demand Tasks Network

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

Oskaloosa, IA

$2,200 - $4,400

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Oskaloosa, IA

$4,250 - $7,225

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Oskaloosa, IA

$2,548 - $4,550

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Oskaloosa, IA

$2,520 - $4,410

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Oskaloosa, IA

$3,185 - $5,460

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Oskaloosa, IA

$3,300 - $6,050

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Oskaloosa, IA

$2,800 - $4,800

United Parcel Service (UPS)

UPS Package Delivery Driver

Oskaloosa, IA

$4,600 - $8,625

Domino's Pizza

Domino's Pizza is hiring a Pizza Delivery Driver in Oskaloosa

Oskaloosa, IA

$2,700 - $4,536

Amazon DSP

Oskaloosa:Delivery Driver(Full-time,$3.5k-$4.8k/Month) | Hiring

Oskaloosa, IA

$3,500 - $4,800

Driving Jobs in Oskaloosa — FAQ

How many driving jobs are available in Oskaloosa, IA right now?
There are currently 20+ open driving positions in Oskaloosa, 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 Oskaloosa?
Driving job pay in Oskaloosa 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 Oskaloosa?
Yes. Many delivery driver, courier, and DSP positions in Oskaloosa 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 Oskaloosa?
Driving jobs in Oskaloosa 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 Oskaloosa?
Benefits vary by employer, but many driving positions in Oskaloosa 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 Oskaloosa?
Your take-home pay as a driver in Oskaloosa 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 Oskaloosa?
Yes, many driving positions in Oskaloosa 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 20+ listings above and apply directly.

Last updated: September 11, 2026