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CDL Jobs in Milwaukee, WI

Browse a wide selection of our CDL jobs in Milwaukee, WI — see how much you can earn and what kind of trucks you’ll be driving.

Trucking Jobs in Milwaukee

We offer a range of truck driving jobs to apply to as a commercial driver.
Enter your ZIP code below to see which CDL A driver jobs are available in your area.

Dry Van Flatbed Hazmat & Doubles Lease & Owner Operator

Dry Van

DRY VAN TRUCKING JOB IN MILWAUKEE, WI

60 CPM
$1,600
Home EVERY
2 – 4 WEEKS

No touch freight

10 CPM Safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW
See more

REGIONAL TRUCK DRIVER JOB IN MILWAUKEE, WI

65 CPM
$1,200
Home
weekly

No touch freight

Health, dental, vision, 401k, paid time off

Orientation, clean inspection pay, and referral bonus

Detailed pay scale and benefits

APPLY NOW
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Flatbed

FLATBED TRUCKING JOB IN MILWAUKEE, WI

65 CPM
$1,725
Home every
2 – 4 weeks

$2,500 sign-on bonus

5 CPM bonus on 11k+ miles monthly

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW
See more

Our Fleet

Our fleet has 500+ modern trucks ready to haul freight across the country. We meet the diverse needs of our clients and ensure every load is delivered on time and without delays.

Our Trucks for Trucking Jobs in Milwaukee and Other Regions Include Practical Features for Trips of Any Distance.

  • Spacious, high-roof cabin
  • Inverter
  • Powerful diesel APU
  • Minifridge
  • Automatic or manua
  • Removable rider seat
  • Comfortable combo sleeper

We have our own maintenance shop with skilled mechanics. It’s stocked with spare parts and everything needed to keep trucks and trailers in top shape.

Apply now
Comfortable combo sleeper 579
Comfortable combo sleeper 567

What’s Special About Being a Driver at HMD?

Based in Chicago, we are a leading transportation company offering trucking jobs in Milwaukee and throughout the United States. We’re always looking for reliable drivers from all over the country to join our team.

Key benefits for drivers

New trucks paired with high-quality trailers

Comprehensive health coverage, including dental, vision, and 401(k)

Supportive back office available 24/7 to assist you

A few real stats coming directly from our drivers

79%

of drivers say they are extremely satisfied with our dispatch service

81%

chose our CDL A driving positions because of strong communication with recruiters

87%

appreciate the high-quality maintenance of our trucks

Become Part of HMD with Truck Driver Jobs in Milwaukee, WI

Use your CDL to build a stable, well-paid career. Our trucking jobs in Milwaukee offer great pay and benefits. We have options that match your skills, experience, and endorsements.

Apply Now

How Much Can You Earn with HMD

Use the section below to see how much you can earn as a company driver with HMD Trucking. Browse our CDL Class A vacancies and check out real paycheck examples from our top drivers.

OTR Dry Van Solo

OTR Dry Van Solo

May 2025

Ennio K.

Miles
13,290
Base CPM, $
0.60
Pay, $
7,974
Bonus pay CPM, $
0.10
Bonus pay, $
1,329
Total, $
9,303

Roman K.

Miles
12,427
Base CPM, $
0.60
Pay, $
7,456
Bonus pay CPM, $
0.08
Bonus pay, $
994
Total, $
8,450

Chris B.

Miles
14,530
Base CPM, $
0.60
Pay, $
8,718
Bonus CPM, $
0.08
Pay, $
1,162
Total, $
9,880
OTR Flatbed Solo

OTR Flatbed Solo

May 2025

Michael W.

Miles
15,128
Base CPM, $
0.65
Pay, $
9,833
Bonus pay CPM, $
0.05
Bonus pay, $
756
Load pay, $
630
Total, $
11,219

Muchael R.

Miles
13,827
Base CPM, $
0.65
Pay, $
8,988
Bonus pay CPM, $
0.05
Bonus pay, $
691
Load pay, $
510
Total, $
10,189
Regional Dry Van Solo

Regional Dry Van Solo

May 2025

Harold A.

Miles
10,490
Base CPM, $
0.65
Pay, $
7,868
Total, $
7,868

Austin P.

September 2023
Miles
9,080
Base CPM, $
0.65
Pay, $
5,902
Total, $
5,902

Ryan N.

September 2023
Miles
9,790
Base CPM, $
0.65
Pay, $
6,364
Total, $
6,364
APPLY NOW

Think this could be a good fit? Click the link to apply for one of our truck driver jobs in Milwaukee, Wisconsin.

APPLY NOW

Think this could be a good fit? Click the link to apply for one of our truck driver jobs in Milwaukee, Wisconsin.

About HMD Trucking

HMD Trucking started in 1998 as a small family business. Today, we are one of the top freight carriers in Chicago, Illinois, and across the United States.

Our fleet includes over 500 modern semi trucks, all equipped to handle a wide range of freight. We provide different hauling services to meet the needs of our clients and continue to grow in new regions.

Find steady, well-paid CDL jobs in Milwaukee, WI with our company.

More on HMD Trucking

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