Driving Jobs in Oshkosh, WI — Now Hiring

As of October 2026, there are 50+ open driving jobs in Oshkosh, WI. Current pay ranges from $17 to $148,500 per year. Top hiring areas include Delivery Driver, Owner Operator and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Oshkosh, WI

$2,800 - $5,000

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Oshkosh, WI

$3,500 - $6,000

United Parcel Service (UPS)

UPS Package Delivery Driver

Oshkosh, WI

$3,640 - $6,825

Auto Logistics Pros

Oshkosh Needs:Driver Opportunity(Part-Time)

Oshkosh, WI

$2,800 - $4,800

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Oshkosh, WI

$3,675 - $6,300

Corporate Catering Couriers

Flexible Hours:Driver Opportunity-Oshkosh

Oshkosh, WI

$3,500 - $6,000

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Oshkosh, WI

$3,000 - $5,500

Secure Document Couriers

[Part-Time] Night Shift Legal/document Courier-Oshkosh

Oshkosh, WI

$2,800 - $5,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Oshkosh, WI

$3,219 - $5,520

On-Demand Tasks Network

Oshkosh Job:Driver Opportunity(No Exp Req*)

Oshkosh, WI

$2,000 - $4,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Oshkosh, WI

$2,300 - $4,140

Heavy Freight Logistics

[Part-Time] Cargo Van / Box Truck Specialist-Oshkosh

Oshkosh, WI

$5,000 - $8,500

Driving Jobs in Oshkosh — FAQ

How many driving jobs are available in Oshkosh, WI right now?
There are currently 50+ open driving jobs in Oshkosh, WI. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Oshkosh?
Pay in Oshkosh depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Oshkosh with no experience?
Yes. Many employers in Oshkosh run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Oshkosh that is home every night?
Local routes in Oshkosh are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Oshkosh?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Oshkosh?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Oshkosh?
Many carriers, delivery firms and local fleets in Oshkosh hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 50+ open routes above and apply directly.

Last updated: October 28, 2026