Driving Jobs in Milwaukee, WI — Open Positions

As of April 2026, there are 230+ open driving positions in Milwaukee, WI. Current pay ranges from $460 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.

Uber

Join Uber in Milwaukee as a Night Shift Driver | Hiring

Milwaukee, WI

$3,200 - $5,500

Instacart

Instacart Full-Service Shopper

Milwaukee, WI

$2,125 - $3,825

Uber

Recruiting:Black Driver in Milwaukee,WI | Hiring

Milwaukee, WI

$4,500 - $7,500

Textile Transit Co.

Industrial Linen & Laundry Route Driver(PT)-Milwaukee,WI

Milwaukee, WI

$4,000 - $5,800

DoorDash

Suburban Route DoorDash Driver

Milwaukee, WI

$2,040 - $3,570

Grubhub

Grubhub Shop and Pay Driver

Milwaukee, WI

$2,380 - $4,080

J.B. Hunt Transport

Milwaukee Flexible Role:J.B. Hunt Regional Intermodal Driver

Milwaukee, WI

$5,500 - $8,500

Uber

Flexible Gig:Ubereats Large Order Delivery Driver(Milwaukee) | Hiring

Milwaukee, WI

$3,500 - $6,000

Mobile Tool Networks

Mobile Tool Sales Route Driver(PT)-Milwaukee,WI

Milwaukee, WI

$4,500 - $8,000

Healthway Logistics

Independent Medical Specimen Courier

Milwaukee, WI

$2,850 - $4,750

Shipt

(Milwaukee)Part-Time:Bulk Order Specialist

Milwaukee, WI

$3,200 - $5,500

Uber

Uber is hiring a Uberx Driver in Milwaukee | Apply Now

Milwaukee, WI

$3,240 - $5,400

Driving Jobs in Milwaukee — FAQ

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

Last updated: April 17, 2026