Driving Jobs in Chesapeake, VA — Open Positions

As of October 2026, there are 20+ open driving jobs in Chesapeake, VA. Current pay ranges from $32 to $364,000 per year. Top hiring areas include Delivery Driver, Cdl A and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Nightline Freight

Part-Time Job in Chesapeake – Overnight Parcel Transfer Driver

Chesapeake, VA

$3,960 - $5,720

Peak Season Logistics

Part-Time Seasonal Holiday Package Driver Job in Chesapeake

Chesapeake, VA

$2,975 - $4,250

Metro Parcel Delivery

Part-Time Urban Step Van Courier – Chesapeake VA | Part Time Job

Chesapeake, VA

$3,458 - $5,005

Health Transit Logistics

Local Part-Time Medical & Pharmacy Package Courier Job –

Chesapeake, VA

$2,944 - $4,140

Weekend Transit Co.

Evening Part-Time Weekend Parcel Delivery Driver – Chesapeake

Chesapeake, VA

$1,650 - $2,750

Heavy Haul Last Mile

Part-Time Heavy/bulky Item Delivery Specialist|Chesapeake,VA

Chesapeake, VA

$3,800 - $5,500

Corporate Courier Logistics

Part-Time B2B Route Logistics Driver Job in Chesapeake | Part

Chesapeake, VA

$2,816 - $4,224

Flex Delivery Network

Part-Time Independent Parcel Courier – Chesapeake VA | Part Time

Chesapeake, VA

$2,240 - $4,480

E-Comm Transit Solutions

Immediate Part-Time E-commerce Delivery Specialist Job –

Chesapeake, VA

$2,816 - $4,224

Local Logistics Pros

Part-Time Local Package Delivery Driver – Chesapeake(Join Team)

Chesapeake, VA

$2,760 - $4,140

Schneider National

CDL A Truck Driver - OTR Dry Van

Chesapeake, VA

$78,750 - $100,800

Crete Carrier

CDL A Truck Driver - Regional Dry Van Home Weekly

Chesapeake, VA

$75,600 - $96,600

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 20+ open driving jobs in Chesapeake, VA. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Chesapeake?
Pay in Chesapeake depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Chesapeake with no experience?
Yes. Many employers in Chesapeake run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Chesapeake that is home every night?
Local routes in Chesapeake are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Chesapeake?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Chesapeake?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Chesapeake?
Many carriers, delivery firms and local fleets in Chesapeake hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 20+ open routes above and apply directly.

Last updated: October 05, 2026