Driving Jobs in Waukesha, WI — Apply Today

As of October 2026, there are 50+ open driving jobs in Waukesha, WI. Current pay ranges from $22 to $155,250 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.

Urban Pedal Logistics

Earn Extra Cash:Driver Opportunity(Waukesha)

Waukesha, WI

$2,500 - $4,500

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Waukesha, WI

$2,500 - $4,500

Corporate Catering Couriers

(Waukesha)Part-Time:Driver Opportunity

Waukesha, WI

$3,500 - $6,000

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Waukesha, WI

$2,400 - $4,200

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Waukesha, WI

$2,380 - $4,250

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Waukesha, WI

$2,464 - $4,224

Heavy Freight Logistics

(Waukesha)Part-Time:Cargo Van / Box Truck Specialist

Waukesha, WI

$5,000 - $8,500

FedEx

(Waukesha)Part-Time:Driver Opportunity

Waukesha, WI

$3,500 - $6,500

Local Merchant Delivery Network

Earn Extra Cash:Early Morning Bakery/floral(Waukesha)

Waukesha, WI

$2,400 - $4,200

Final Mile Delivery Co.

Hiring in Waukesha:Final Mile Parcel(Part-Time)

Waukesha, WI

$3,000 - $5,500

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Waukesha, WI

$4,400 - $7,480

Secure Document Couriers

(Waukesha)Part-Time:Night Shift Legal/document Courier

Waukesha, WI

$2,800 - $5,000

Driving Jobs in Waukesha — FAQ

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