Driving Jobs in Oskaloosa, IA — See Openings

As of April 2026, there are 30+ open driving positions in Oskaloosa, IA. Current pay ranges from $680 to $8,500 per year. Top hiring areas include Delivery Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Oskaloosa Independent Contractor Driver-Long Distance / Regional

Oskaloosa, IA

$3,500 - $6,000

Midday Logistics Co.

[Part-Time] Driver Opportunity-Oskaloosa

Oskaloosa, IA

$1,050 - $2,100

Heavy Freight Logistics

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

Oskaloosa, IA

$5,000 - $8,500

United Parcel Service (UPS)

UPS Package Delivery Driver Needed-Oskaloosa Area | Hiring

Oskaloosa, IA

$4,000 - $7,500

Grubhub

Suburban Route Grubhub Driver

Oskaloosa, IA

$2,592 - $4,536

Grubhub

Campus Area Grubhub Driver

Oskaloosa, IA

$2,912 - $5,376

Campus Courier Network

Driver Opportunity needed in Oskaloosa(Apply Now)

Oskaloosa, IA

$2,600 - $4,800

FreshDrop Logistics

Start ASAP:Driver Opportunity(Oskaloosa)

Oskaloosa, IA

$3,000 - $5,500

Corporate Catering Couriers

Oskaloosa Career:Independent Contractor Driver-Catering Logistics at

Oskaloosa, IA

$3,500 - $6,000

National Grocery Delivery Network

Evening Role:Driver Opportunity(Oskaloosa)

Oskaloosa, IA

$2,625 - $4,725

Local Merchant Delivery Network

Oskaloosa-based Independent Contractor Driver-Early Morning

Oskaloosa, IA

$2,400 - $4,200

Suburban Delivery Network

$43.75/hr Driver Opportunity-Oskaloosa(PT)

Oskaloosa, IA

$2,800 - $4,800

Driving Jobs in Oskaloosa — FAQ

How many driving jobs are available in Oskaloosa, IA right now?
There are currently 30+ 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 30+ listings above and apply directly.

Last updated: April 26, 2026