Driving Jobs in Waukesha, WI — Start This Week

As of May 2026, there are 240+ open driving positions in Waukesha, WI. Current pay ranges from $425 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.

Shipt

Evening & Night Shift Courier(Part-Time)@ Shipt-Waukesha

Waukesha, WI

$2,800 - $4,800

Last Mile Logistics Network

Independent Contractor Driver - Last-Mile Logistics

Waukesha, WI

$3,080 - $5,500

Fresh Crust Logistics

$49.00/hr Driver Opportunity-Waukesha(PT)

Waukesha, WI

$3,500 - $5,000

Instacart

Instacart Full-Service Shopper

Waukesha, WI

$2,125 - $3,825

Local Merchant Delivery Network

Join Local Merchant Delivery Network in Waukesha as a Independent

Waukesha, WI

$2,400 - $4,200

E-Comm Transit Solutions

Part-Time E-commerce Delivery Specialist – Waukesha WI | Part

Waukesha, WI

$3,360 - $5,040

XPO Logistics

Waukesha Flexible Role:Local City Driver

Waukesha, WI

$5,000 - $8,000

Local Shopper Partners

Start ASAP:Courier(Waukesha)

Waukesha, WI

$2,000 - $3,500

Grubhub

Grubhub Large Order Delivery Driver

Waukesha, WI

$3,850 - $6,600

United Parcel Service (UPS)

Weekend Shift:Driver Opportunity-Waukesha

Waukesha, WI

$4,500 - $8,000

Peak Season Logistics

Part-Time Seasonal Holiday Package Driver Job – Waukesha Hiring

Waukesha, WI

$3,080 - $4,400

Instacart

Urban E-Bike Instacart Courier

Waukesha, WI

$2,625 - $4,725

Driving Jobs in Waukesha — FAQ

How many driving jobs are available in Waukesha, WI right now?
There are currently 240+ 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 240+ listings above and apply directly.

Last updated: May 08, 2026