Driving Jobs in Waukesha, WI — Immediate Openings

As of April 2026, there are 140+ open driving positions in Waukesha, WI. Current pay ranges from $500 to $9,520 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

Grubhub Delivery Driver

Waukesha, WI

$2,275 - $4,095

Instacart

Urban E-Bike Instacart Courier

Waukesha, WI

$2,500 - $4,500

DoorDash

Night Shift DoorDash Driver (Late Night Logistics)

Waukesha, WI

$2,380 - $4,080

Uber

Weekend Ubereats Delivery Professional Position in Waukesha | Hiring

Waukesha, WI

$2,200 - $3,800

Uber

Join Team in Waukesha:Night Shift Rideshare Driver | Hiring

Waukesha, WI

$3,200 - $5,500

Grubhub

Weekend Part-Time Suburban Route Driver – Waukesha | Part Time

Waukesha, WI

$2,400 - $4,200

Lyft

Join Lyft in Waukesha as a Premium Rideshare Driver | Hiring

Waukesha, WI

$4,500 - $7,500

Uber

Weekend Ubereats Delivery Professional(Gig)-Waukesha

Waukesha, WI

$2,420 - $4,180

Shipt

Dedicated Shopper needed in Waukesha(Apply Now)

Waukesha, WI

$3,000 - $5,500

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Waukesha, WI

$2,160 - $4,320

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Waukesha, WI

$3,024 - $5,400

Uber

Waukesha Ubereats Bicycle & Scooter Courier(Gig)

Waukesha, WI

$2,500 - $4,500

Driving Jobs in Waukesha — FAQ

How many driving jobs are available in Waukesha, WI right now?
There are currently 140+ 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 140+ listings above and apply directly.

Last updated: April 26, 2026