Driving Jobs in Chesapeake, VA — Apply Today

As of October 2026, there are 180+ open driving jobs in Chesapeake, VA. Current pay ranges from $16 to $364,000 per year. Top hiring areas include Delivery Driver, Cdl A and Owner Operator. New roles are posted daily — listings on this page are verified and updated regularly.

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Chesapeake, VA

$94,500 - $126,000

MTA New York City Transit

Transit Bus Driver - CDL B Public Transportation

Chesapeake, VA

$30 - $42

Regional Auto Dealership Group

Chesapeake Full-time OEM Dealership Auto Parts Delivery Driver

Chesapeake, VA

$3,000 - $4,500

FedEx Custom Critical

Expedited Sprinter Van Driver - Time Critical Cargo

Chesapeake, VA

$69,000 - $124,200

Ferguson HVAC

HVAC Parts Delivery Driver And Warehouse Associate Needed-Chesapeake

Chesapeake, VA

$16 - $22

US Foods

Restaurant Supply Delivery Driver-CDL Class

Chesapeake, VA

$22 - $30

FedEx

Earn Extra Cash:Driver Opportunity(Chesapeake)

Chesapeake, VA

$3,500 - $6,500

Ferguson HVAC

HVAC Parts Delivery Driver And Warehouse Associate-Chesapeake,VA

Chesapeake, VA

$20 - $28

Southern Glazer's Wine & Spirits

Chesapeake Wine And Spirits Delivery Driver-CDL Class

Chesapeake, VA

$25 - $32

Levin Furniture and Mattress

VA Career:Mattress Delivery Driver-2 Person Team Home Setup in

Chesapeake, VA

$16 - $21

O'Reilly Auto Parts

O'reilly Auto Parts(Chesapeake)Hiring:Delivery Driver & Logistics

Chesapeake, VA

$2,800 - $4,000

Pella Windows and Doors

Chesapeake Glass And Window Delivery Driver-CDL B Flatbed($20-$25/hr)

Chesapeake, VA

$20 - $25

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 180+ 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 180+ open routes above and apply directly.

Last updated: October 29, 2026