OTR Dry Van Solo
$1,625Gross Weekly Avg.
65 CPMAll Miles
2–4 weeksHome every
$2,500 sign-on bonus
10 CPM Safety/ productivity bonus
Health, dental, vision, 401k, paid time off
Truck Driving 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
Enter your ZIP code below to see which CDL A driver jobs are available in your area.
Dry Van
Regional Dry Van Solo
$1,260Gross Weekly Avg.
70 CPMAll miles
WeeklyHome time
$2,500 sign-on bonus
Health, dental, vision, 401k, paid time off
Orientation, clean inspection pay, and referral bonus
Flatbed
OTR Flatbed Solo
$1,750Gross Weekly Avg.
70 CPMAll miles
2 – 4 WeeksHome every
$5,000 sign-on bonus
10 CPM bonus on 11.5k+ miles monthly
Health, dental, vision, 401k, paid time off
Our Fleet
Our fleet includes over 650 modern trucks ready to haul freight across the country. Trucks used in trucking jobs in Milwaukee and other regions come equipped with practical features for trips of any distance.
HMD Trucking semi trucks come with the following features:
Peterbilt
Spacious, high-roof cabin
Inverter
Powerful diesel APU
Minifridge
Automatic
Removable rider seat
Comfortable combo sleeper
HMD Trucking Company Started as a Family Business in Chicago, Illinois, Back in 1998
What began as a small operation has grown into a nationwide carrier with a strong presence in Chicago and across the United States. Today, HMD Trucking operates a fleet of over 650 modern semi trucks, built to handle a wide range of freight and keep drivers moving consistently.
We continue to expand into new regions while maintaining steady freight and reliable routes. Join our team for CDL jobs in Milwaukee, WI.
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. Think this could be a good fit? Click the link to apply for one of our truck driver jobs in Milwaukee, Wisconsin.
Apply nowRegional Dry Van Solo
May 2026Harold A.
Miles Dry Van10,490
Base CPM$0.70
Base Pay$7,343
Total$7,343
Austin P.
Miles Dry Van9,080
Base CPM$0.70
Base Pay$6,356
Total$6,356
Ryan N.
Miles Dry Van9,790
Base CPM$0.70
Base Pay$6,853
Total$6,853
What’s Special About Being a Driver at HMD?
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
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.
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.
Recruiting: 888 215 8523
By clicking "Apply Now", you agree that HMD Trucking may contact you by phone and email regarding your driver application. You also agree to our Terms of Service and Privacy Policy.
HMD Trucking Blog
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Learn how cybercriminals hijack carrier authority to steal high-value freight, your legal liability risks, and how to protect your fleet.
Understanding Fentanyl and DOT Drug Test Requirements in 2026
Learn how new DOT rules for truck drivers impact fentanyl testing, MRO reviews, and CDL compliance. Stay ahead with HMD Trucking's guide.
Cyber Security Incident Reporting: What CIRCIA Means for Fleets
Learn how CIRCIA reporting rules and new federal mandates are redefining cybersecurity in trucking for mid-sized commercial fleets.
Defending Against Cargo Theft: The Threat of Deepfakes and GPS Spoofing
HMD Trucking shares vital defense strategies against AI-driven cargo theft, voice deepfakes, and GPS spoofing in OTR freight.
FMCSA English Requirement: Bracing for Stricter DOT Enforcement
Discover how the new FMCSA English requirement turns language checks into out-of-service violations and has impacted over 10,000 drivers in 2026.
The 2026 Broker Transparency Rule: A Battle for Honest Freight Loads
Learn how the 2026 FMCSA broker transparency rule aims to protect small fleets from income theft and create a fairer market.
Navigating the FMCSA Motus Registration System and the End of MC Numbers
Learn how the FMCSA Motus registration system uses USDOT suffixes to simplify compliance and stop chameleon carrier fraud.
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