Driving Jobs in Milwaukee, WI — Hiring Now

As of May 2026, there are 160+ open driving positions in Milwaukee, WI. Current pay ranges from $12 to $320,320 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Sysco

Sysco Foodservice Delivery Driver - CDL A Home Daily

Milwaukee, WI

$77,350 - $95,550

FedEx

Join Team:Ground Delivery Driver(Flexible,Milwaukee)

Milwaukee, WI

$18 - $22

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Milwaukee, WI

$3,185 - $5,460

Amazon DSP

Amazon DSP Delivery Driver

Milwaukee, WI

$3,850 - $5,280

Shipt

Flexible Hours:Driver Opportunity-Milwaukee

Milwaukee, WI

$16 - $22

Canteen

Part-Time Job in Milwaukee:Vending Machine Delivery Driver And

Milwaukee, WI

$18 - $24

DoorDash

Join Doordash in Milwaukee as a Delivery Driver-Food Delivery Part

Milwaukee, WI

$15 - $22

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Milwaukee, WI

$5,500 - $9,350

Stevens Trucking

Urgent Hire in Milwaukee:Driver Opportunity

Milwaukee, WI

$85,000 - $115,000

Quest Diagnostics

Flexible Gig:Delivery Driver-Medical Courier Pharmaceuticals

Milwaukee, WI

$20 - $26

Quest Diagnostics

Medical Courier Delivery Driver

Milwaukee, WI

$2,800 - $4,200

Final Mile Delivery Co.

Immediate Opening in Milwaukee for a Independent Contractor

Milwaukee, WI

$3,000 - $5,500

Driving Jobs in Milwaukee — FAQ

How many driving jobs are available in Milwaukee, WI right now?
There are currently 160+ 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 160+ listings above and apply directly.

Last updated: May 13, 2026