Driving Jobs in Milwaukee, WI — See Openings

As of May 2026, there are 50+ open driving positions in Milwaukee, WI. Current pay ranges from $14 to $103,500 per year. Top hiring areas include Delivery Driver, Cdl Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Delivery Driver-Package Handler-Milwaukee,WI | Hiring

Milwaukee, WI

$21 - $26

Domino's Pizza

Milwaukee Delivery Driver-Pizza Delivery Tips Plus Wages with

Milwaukee, WI

$14 - $20

Wayfair

$21-$27/hr Delivery Driver-Furniture And Appliance Home Installation

Milwaukee, WI

$21 - $27

Quest Diagnostics

Work in Milwaukee:Delivery Driver-Medical Courier Pharmaceuticals

Milwaukee, WI

$20 - $26

XPO Logistics

XPO Logistics Needs Delivery Driver-Package Handler Box Truck in

Milwaukee, WI

$22 - $28

Instacart

Milwaukee Part-time Delivery Driver-Grocery Same Day Service | Hiring

Milwaukee, WI

$16 - $23

Schneider National

Milwaukee:Delivery Driver-CDL Class A Regional Routes

Milwaukee, WI

$70,000 - $85,000

DoorDash

Delivery Driver-Food Delivery Part Time Evenings•Milwaukee,WI•Doordash

Milwaukee, WI

$15 - $22

Amazon Flex

Amazon Flex Needs Delivery Driver-Independent Contractor in Milwaukee

Milwaukee, WI

$18 - $25

Express Logistics

Milwaukee Career:Delivery Driver-Full Time Local Routes at Express

Milwaukee, WI

$19 - $24

Roadie

Box Truck Delivery Driver

Milwaukee, WI

$4,500 - $7,800

Uber Eats

Daily Pay Delivery Driver

Milwaukee, WI

$3,024 - $5,184

Driving Jobs in Milwaukee — FAQ

How many driving jobs are available in Milwaukee, WI right now?
There are currently 50+ open driving positions in Milwaukee, 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 Milwaukee?
Driving job pay in Milwaukee 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 Milwaukee?
Yes. Many delivery driver, courier, and DSP positions in Milwaukee 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 Milwaukee?
Driving jobs in Milwaukee 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 Milwaukee?
Benefits vary by employer, but many driving positions in Milwaukee 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 Milwaukee?
Your take-home pay as a driver in Milwaukee 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 Milwaukee?
Yes, many driving positions in Milwaukee 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 50+ listings above and apply directly.

Last updated: May 10, 2026