Driving Jobs in Milwaukee, WI — Now Hiring

As of October 2026, there are 50+ open driving jobs in Milwaukee, WI. Current pay ranges from $20 to $145,800 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.

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Milwaukee, WI

$2,800 - $4,800

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Milwaukee, WI

$3,000 - $5,500

Auto Logistics Pros

Driver Opportunity needed in Milwaukee(Apply Now)

Milwaukee, WI

$2,800 - $4,800

Secure Document Couriers

Weekend Shift:Night Shift Legal/document Courier-Milwaukee

Milwaukee, WI

$2,800 - $5,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Milwaukee, WI

$2,700 - $4,860

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Milwaukee, WI

$2,640 - $4,620

Urban Pedal Logistics

Evening Role:Driver Opportunity(Milwaukee)

Milwaukee, WI

$2,500 - $4,500

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Milwaukee, WI

$5,000 - $8,500

Corporate Catering Couriers

Urgent Hire in Milwaukee:Driver Opportunity

Milwaukee, WI

$3,500 - $6,000

FedEx

Earn Extra Cash:Driver Opportunity(Milwaukee)

Milwaukee, WI

$3,500 - $6,500

Local Merchant Delivery Network

Early Morning Bakery/floral(Part-Time)@ Local Merchant Delivery Network-Mil...

Milwaukee, WI

$2,400 - $4,200

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Milwaukee, WI

$3,220 - $5,520

Driving Jobs in Milwaukee — FAQ

How many driving jobs are available in Milwaukee, WI right now?
There are currently 50+ open driving jobs in Milwaukee, 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 Milwaukee?
Pay in Milwaukee 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 Milwaukee with no experience?
Yes. Many employers in Milwaukee 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 Milwaukee that is home every night?
Local routes in Milwaukee 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 Milwaukee?
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 Milwaukee?
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 Milwaukee?
Many carriers, delivery firms and local fleets in Milwaukee 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