Driving Jobs in Waukesha, WI — Open Positions

As of April 2026, there are 230+ open driving positions in Waukesha, WI. Current pay ranges from $455 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Waukesha-based Independent Contractor Driver-Long Distance / Regional

Waukesha, WI

$3,500 - $6,000

Uber

Recent Job Weekend Rideshare Driver @ Uber in Waukesha | Hiring

Waukesha, WI

$2,000 - $3,500

Local Logistics Pros

Part-Time Job in Waukesha:Local Package Delivery Driver | Part

Waukesha, WI

$3,300 - $4,950

XPO Logistics

XPO Logistics LTL Box Truck Driver (City P&D)

Waukesha, WI

$4,800 - $7,200

United States Postal Service

Seasonal Postal Delivery Worker

Waukesha, WI

$3,000 - $5,500

Night Owl Expedite

Overnight Regional Expedite Courier (Hot Shot)

Waukesha, WI

$3,990 - $6,090

United Parcel Service (UPS)

Waukesha-based UPS Package Delivery Driver Opening | Hiring

Waukesha, WI

$4,000 - $7,500

Shipt

$43.75/hr Suburban Route Shopper-Waukesha(PT)

Waukesha, WI

$2,800 - $4,800

Shipt

Urgent Hire in Waukesha:Early Morning Shopper

Waukesha, WI

$2,200 - $3,800

SnackRoute Solutions

Driver Opportunity needed in Waukesha(Apply Now)

Waukesha, WI

$3,200 - $4,800

Instacart

Suburban Instacart Shopper

Waukesha, WI

$2,464 - $4,224

Midnight Logistics

[Part-Time] Late Night Convenience & Grocery Courier-Waukesha

Waukesha, WI

$2,800 - $4,800

Driving Jobs in Waukesha — FAQ

How many driving jobs are available in Waukesha, WI right now?
There are currently 230+ 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 230+ listings above and apply directly.

Last updated: April 17, 2026