Driving Jobs in Oskaloosa, IA — See Openings

As of May 2026, there are 50+ open driving positions in Oskaloosa, IA. Current pay ranges from $550 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.

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Oskaloosa, IA

$2,548 - $4,550

Heavy Freight Logistics

Oskaloosa Independent Contractor Driver-Cargo Van / Box Truck

Oskaloosa, IA

$5,000 - $8,500

Task & Dash Couriers

On-Demand Local Courier (Gig Economy)

Oskaloosa, IA

$2,000 - $4,000

On-Demand Tasks Network

Join Team:Independent Contractor Driver-On-demand Errands in

Oskaloosa, IA

$2,000 - $4,000

Uber

Apply Now:Ubereats Bicycle & Scooter Courier in Oskaloosa | Hiring

Oskaloosa, IA

$2,500 - $4,500

Regional Expedite Logistics

Regional Expedite Logistics seeks Independent Contractor Driver-Long

Oskaloosa, IA

$3,220 - $5,520

Heavy Route Couriers

Dedicated Route Freight Courier (Cargo Van)

Oskaloosa, IA

$4,000 - $6,000

Auto Logistics Pros

Oskaloosa-based Independent Contractor Driver-Auto Parts Courier

Oskaloosa, IA

$2,800 - $4,800

Mechanic's Choice Transport

Automotive Parts Courier

Oskaloosa, IA

$2,800 - $4,200

Uber

Connect Package Delivery Driver Needed-Oskaloosa Area | Hiring

Oskaloosa, IA

$3,000 - $5,500

Uber

Oskaloosa:Black Driver(Contractor,$4k-$6.6k/Month) | Hiring

Oskaloosa, IA

$3,960 - $6,600

Night Owl Expedite

Overnight Regional Expedite Courier (Hot Shot)

Oskaloosa, IA

$3,800 - $5,800

Driving Jobs in Oskaloosa — FAQ

How many driving jobs are available in Oskaloosa, IA right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: May 03, 2026