Driving Jobs in Milwaukee, WI — Start This Week

As of September 2026, there are 40+ open driving positions in Milwaukee, WI. Current pay ranges from $14 to $128,800 per year. Top hiring areas include Delivery Driver, Cdl Driver and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Atlas Van Lines

CDL A Household Goods Mover Truck Driver

Milwaukee, WI

$97,749 - $126,499

Stevens Trucking

CDL A Livestock Hauler Truck Driver - Cattle Transport

Milwaukee, WI

$95,200 - $128,800

AAA Roadside

CDL B Tow Truck Driver - Heavy Duty Recovery

Milwaukee, WI

$30 - $44

Waste Management

CDL B Garbage Truck Driver - Residential Refuse

Milwaukee, WI

$21 - $28

Cersosimo Lumber Company

CDL A Log Truck Driver - Forestry Hauler

Milwaukee, WI

$25 - $33

Heavy Legacy LLC

CDL A Frac Sand Driver - Oilfield West Texas

Milwaukee, WI

$79,200 - $110,000

SCC Concrete

CDL B Truck Driver - Ready Mix Concrete Mixer

Milwaukee, WI

$25 - $32

Staker Parson Companies

CDL A Dump Truck Driver - Local Aggregate Hauling

Milwaukee, WI

$27 - $34

Old Dominion Freight Line

CDL A Truck Driver - LTL Pickup and Delivery

Milwaukee, WI

$86,400 - $102,600

J.B. Hunt Intermodal

CDL A Truck Driver - Intermodal Container Drayage

Milwaukee, WI

$63,750 - $80,750

Regional Expedite Logistics

Start ASAP:Driver Opportunity(Milwaukee)

Milwaukee, WI

$3,325 - $5,700

Urban Pedal Logistics

$40.50/hr Driver Opportunity-Milwaukee(PT)

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 40+ 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 40+ listings above and apply directly.

Last updated: September 09, 2026