CDL-A Truck Driving Jobs in Milwaukee, WI — Start This Week

As of October 2026, there are 8 cdl-a truck driving openings in Milwaukee, WI. Local pay ranges from $21 to $130,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Matheson Postal Services

USPS Mail Haul Truck Driver - CDL A Contractor

Milwaukee, WI

$70,000 - $90,000

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Milwaukee, WI

$82,800 - $110,400

Penske Logistics

CDL A Yard Hostler Truck Driver - Trailer Spotter

Milwaukee, WI

$21 - $26

Hot Shot Transportation Co.

Hot Shot Truck Driver - Owner Operator with 1 Ton Pickup

Milwaukee, WI

$85,000 - $130,000

Granite Construction

CDL B Water Truck Driver - Construction Site Dust Control

Milwaukee, WI

$23 - $29

XPO Logistics

$4.8k-$7.2k/Month LTL Box Truck Driver job in Milwaukee | Hiring

Milwaukee, WI

$4,800 - $7,200

PepsiCo

Beverage Distribution Box Truck Driver($5k-$7.5k/Month)-Milwaukee,WI

Milwaukee, WI

$5,000 - $7,500

Sysco Corporation

Milwaukee Sysco Foodservice Box Truck Driver(Full-time)-Sysco

Milwaukee, WI

$5,500 - $8,500

CDL-A Truck Driving Jobs in Milwaukee — FAQ

How many cdl-a truck driving jobs are open in Milwaukee, WI?
There are currently 8+ cdl-a truck driving in Milwaukee, WI. New cdl-a truck driving roles are added regularly — check this page for the latest openings.
How much do cdl-a truck driving jobs pay in Milwaukee?
Pay for cdl-a truck driving in Milwaukee varies by employer, equipment and how much time you spend away. Many positions offer flexible scheduling and employee discounts, and some include shift differentials for nights and weekends. Browse the listings above to see pay details for each opening.
Do these cdl-a truck driving positions require experience in Milwaukee?
Many cdl-a truck driving positions in Milwaukee require no prior experience, and most employers provide paid on-the-job training. Check individual listings for specific requirements.
How do I apply for cdl-a truck driving jobs in Milwaukee?
Browse the 8+ cdl-a truck driving listings above, click on any position for full details including pay and shift times, then follow the application link to the employer. Most driver applications take about 10–20 minutes online.

CDL-A Truck Driving Jobs in Other Cities

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CDL-A Truck Driving Jobs in San Diego

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CDL-A Truck Driving Jobs in Dallas

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CDL-A Truck Driving Jobs in Fort Worth

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Other Driving Careers in Milwaukee

Full-Time Driving Jobs in Milwaukee

29 open positions

Part-Time Driving Jobs in Milwaukee

25 open positions

Delivery Driver Jobs in Milwaukee

21 open positions

CDL-B Driving Jobs in Milwaukee

13 open positions

Box Truck & Straight Truck Jobs in Milwaukee

12 open positions

Weekend Driving Jobs in Milwaukee

10 open positions

Owner Operator & Lease Purchase in Milwaukee

9 open positions

Regional Driving Jobs in Milwaukee

7 open positions

Last updated: October 29, 2026