Driving Jobs in Milwaukee, WI — Immediate Openings

As of May 2026, there are 240+ open driving positions in Milwaukee, WI. Current pay ranges from $500 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.

Paws In Motion Mobile

Driver Opportunity(Part-Time)@ Paws In Motion Mobile-Milwaukee

Milwaukee, WI

$4,000 - $6,500

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Milwaukee, WI

$3,449 - $6,324

Grubhub

Weekend Grubhub Delivery Professional

Milwaukee, WI

$1,870 - $3,230

United States Postal Service

Rural Carrier Associate (RCA)

Milwaukee, WI

$3,094 - $4,368

ProWear Logistics

Earn Extra Cash:Driver Opportunity(Milwaukee)

Milwaukee, WI

$3,800 - $5,500

DoorDash

DoorDash Large Order (Catering) Driver

Milwaukee, WI

$3,185 - $5,460

Peak Season Logistics

Immediate Part-Time Seasonal Holiday Package Driver Job –

Milwaukee, WI

$2,975 - $4,250

Auto Logistics Pros

Milwaukee Career:Independent Contractor Driver-Auto Parts Courier at

Milwaukee, WI

$2,800 - $4,800

Task & Dash Couriers

On-Demand Local Courier (Gig Economy)

Milwaukee, WI

$2,000 - $4,000

Regional Expedite Logistics

Milwaukee Independent Contractor Driver-Long Distance / Regional

Milwaukee, WI

$3,220 - $5,520

J.B. Hunt Transport

Milwaukee Contract:J.B. Hunt Regional Intermodal Driver

Milwaukee, WI

$5,500 - $8,500

Shipt

Flexible Hours:Driver Opportunity-Milwaukee

Milwaukee, WI

$2,500 - $4,500

Driving Jobs in Milwaukee — FAQ

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

Last updated: May 08, 2026