Driving Jobs in Waukesha, WI — See Openings

As of May 2026, there are 180+ open driving positions in Waukesha, WI. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Part-Time Weekend Delivery Professional(Waukesha,WI)|Grubhub

Waukesha, WI

$2,200 - $3,800

Grubhub

Part-Time Part-time Driver(lunch Rush)– Waukesha(Now Hiring)

Waukesha, WI

$800 - $1,800

DHL Express

Flexible Courier Driver(Waukesha)

Waukesha, WI

$3,600 - $5,200

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Waukesha, WI

$2,940 - $5,040

Uber

Event Driver Needed-Waukesha Area | Hiring

Waukesha, WI

$3,136 - $5,600

Grubhub

Weekend Part-Time Early Morning Driver – Waukesha | Part Time Job

Waukesha, WI

$2,200 - $3,800

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Waukesha, WI

$5,250 - $8,925

Urban Pedal Logistics

Waukesha:Independent Contractor Driver-Urban E-bike/scooter Courier

Waukesha, WI

$2,500 - $4,500

DoorDash

Suburban Route DoorDash Driver

Waukesha, WI

$2,184 - $3,822

Uber

Flexible Gig:Ubereats Large Order Delivery Driver(Waukesha) | Hiring

Waukesha, WI

$3,500 - $6,000

Uber

Suburban Route Ubereats Driver(Gig Economy And Logistics)Vacancy in

Waukesha, WI

$2,400 - $4,200

Secure Document Couriers

Secure Document Couriers seeks Independent Contractor Driver-Night

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 180+ open driving positions in Waukesha, WI. 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 Waukesha?
Driving job pay in Waukesha 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 Waukesha?
Yes. Many delivery driver, courier, and DSP positions in Waukesha 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 Waukesha?
Driving jobs in Waukesha 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 Waukesha?
Benefits vary by employer, but many driving positions in Waukesha 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 Waukesha?
Your take-home pay as a driver in Waukesha 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 Waukesha?
Yes, many driving positions in Waukesha 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 180+ listings above and apply directly.

Last updated: May 04, 2026