Driving Jobs in Chesapeake, VA — Apply Today

As of October 2026, there are 60+ open driving jobs in Chesapeake, VA. Current pay ranges from $16 to $8,925 per year. Top hiring areas include Delivery Driver, Owner Operator and Flatbed. New roles are posted daily — listings on this page are verified and updated regularly.

US Foods

Restaurant Supply Delivery Driver-CDL Class

Chesapeake, VA

$22 - $30

Pella Windows and Doors

Glass And Window Delivery Driver-CDL B Flatbed|Chesapeake,VA|Pella

Chesapeake, VA

$21 - $27

Bimbo Bakeries USA

Bakery Product Delivery Driver-Independent

Chesapeake, VA

$21 - $29

Canteen

Chesapeake Vending Machine Delivery Driver And Route Service with

Chesapeake, VA

$16 - $21

Levin Furniture and Mattress

Levin Furniture And Mattress is hiring a Mattress Delivery Driver-2

Chesapeake, VA

$21 - $28

Cintas

Cintas(Chesapeake)Hiring:Uniform And Linen Service Delivery Driver

Chesapeake, VA

$24 - $31

Sherwin-Williams

Paint Store Delivery Driver-Commercial

Chesapeake, VA

$18 - $24

Ferguson HVAC

HVAC Parts Delivery Driver And Warehouse Associate Needed-Chesapeake

Chesapeake, VA

$16 - $22

Southern Glazer's Wine & Spirits

Chesapeake:Wine And Spirits Delivery Driver-CDL Class B

Chesapeake, VA

$24 - $30

General Beer Northeast

Work in Chesapeake:Beer Delivery Driver-CDL A Distributor Route

Chesapeake, VA

$22 - $28

US Foods

Work in Chesapeake:Restaurant Supply Delivery Driver-CDL Class B

Chesapeake, VA

$23 - $31

Pella Windows and Doors

Pella Windows And Doors is hiring a Glass And Window Delivery

Chesapeake, VA

$21 - $26

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 60+ 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 60+ open routes above and apply directly.

Last updated: October 28, 2026