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 Chesapeake, VA
Explore truck driving jobs in Chesapeake, VA that fit your experience and career goals.
Trucking Jobs
Enter your ZIP code below to see which CDL A driver jobs are available in your area.
Dry Van
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
Your Truck, Your Workspace
HMD Trucking operates a fleet of over 650 modern trucks designed for diverse freight operations, creating consistent truck driving jobs in Chesapeake, VA, and across major freight lanes nationwide. Whether you’re based in Virginia or anywhere across the country, you’ll be driving safe, well-maintained equipment that’s always ready for the next haul.
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
HMD Trucking began as a family-run operation and has grown into one of the nation’s leading freight carriers. Today, the company operates a fleet of more than 650 modern trucks, ensuring reliable freight movement nationwide while offering trucking jobs in Chesapeake, Virginia, and across the United States.
Learn more about our company and what keeps us moving forward below.
See How Much You Can Earn Driving with HMD
Browse our open vacancies to explore the earning potential of a company driver at HMD. Verified results from our top drivers highlight what you can realistically expect. Think that could be a good fit for you? Great! Click the link to apply for one of our CDL jobs in Chesapeake.
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
Why Drivers Trust HMD Trucking
79%
of our drivers are satisfied with how dispatch organizes and manages their routes.
81%
value the honest, transparent communication they receive during hiring and onboarding.
87%
appreciate the reliability and regular maintenance of our modern trucks.
Based in Chicago, we’re one of the nation’s leading transportation companies, offering a wide range of truck driving jobs in Chesapeake, VA throughout our nationwide network.
Apply Today for Top Trucking Jobs in Trucking Jobs in Chesapeake
Put your commercial driver’s license to good use and start achieving financial stability while enjoying the many benefits that come with our CDL jobs in Chesapeake, . We offer a wide range of commercial driving careers suited to your experience, expertise, and endorsement types.
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
Identity Hijacking: How Cybercriminals Are Stealing Carrier Authority
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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