Driving Jobs in Milwaukee, WI — Open Positions

As of October 2026, there are 22+ open driving jobs in Milwaukee, WI. Current pay ranges from $32 to $345,800 per year. Top hiring areas include Delivery Driver, Cdl A and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Nightline Freight

Student-Friendly Part-Time Overnight Parcel Transfer Driver in

Milwaukee, WI

$3,600 - $5,200

Peak Season Logistics

Part-Time Seasonal Holiday Package Driver Job – Milwaukee Hiring

Milwaukee, WI

$3,500 - $5,000

Metro Parcel Delivery

Part-Time Role in Milwaukee:Urban Step Van Courier | Part Time

Milwaukee, WI

$3,230 - $4,675

Health Transit Logistics

Weekend Part-Time Medical & Pharmacy Package Courier – Milwaukee

Milwaukee, WI

$3,360 - $4,725

Weekend Transit Co.

Part-Time Weekend Parcel Delivery Driver Job in Milwaukee | Part

Milwaukee, WI

$1,320 - $2,200

Heavy Haul Last Mile

Immediate Part-Time Heavy/bulky Item Delivery Specialist Job –

Milwaukee, WI

$3,800 - $5,500

Corporate Courier Logistics

Part-Time B2B Route Logistics Driver(Milwaukee,WI)|Corporate

Milwaukee, WI

$3,200 - $4,800

Flex Delivery Network

Part-Time Independent Parcel Courier – Milwaukee,WI | Part Time

Milwaukee, WI

$2,300 - $4,600

E-Comm Transit Solutions

E-commerce Delivery Specialist|Part-Time Job|Milwaukee | Part

Milwaukee, WI

$3,584 - $5,376

Local Logistics Pros

Evening Part-Time Local Package Delivery Driver – Milwaukee

Milwaukee, WI

$2,640 - $3,960

DoorDash

Milwaukee:Flower Delivery Driver(Contractor,$2.4k-$4.2k/Month)

Milwaukee, WI

$2,400 - $4,200

Instacart

Apply Now:Pet Supply Delivery Driver in Milwaukee | Hiring

Milwaukee, WI

$2,900 - $4,800

Driving Jobs in Milwaukee — FAQ

How many driving jobs are available in Milwaukee, WI right now?
There are currently 22+ 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 22+ open routes above and apply directly.

Last updated: October 05, 2026