Driving Jobs in Chesapeake, VA — Open Positions

As of October 2026, there are 90+ open driving jobs in Chesapeake, VA. Current pay ranges from $16 to $126,000 per year. Top hiring areas include Delivery Driver, Owner Operator and General. New roles are posted daily — listings on this page are verified and updated regularly.

Levin Furniture and Mattress

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

Chesapeake, VA

$16 - $21

General Beer Northeast

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

Chesapeake, VA

$22 - $28

Levin Furniture and Mattress

Join Levin Furniture And Mattress in Chesapeake as a Mattress Delivery

Chesapeake, VA

$17 - $23

Cintas

Uniform And Linen Service Delivery Driver-Chesapeake,VA | Hiring

Chesapeake, VA

$22 - $28

Cintas

Uniform And Linen Service Delivery Driver|Chesapeake,VA|Cintas

Chesapeake, VA

$19 - $24

General Beer Northeast

General Beer Northeast Needs Beer Delivery Driver-CDL A Distributor

Chesapeake, VA

$25 - $32

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Chesapeake, VA

$3,185 - $5,460

Bimbo Bakeries USA

Join Bimbo Bakeries USA in Chesapeake as a Bakery Product Delivery

Chesapeake, VA

$17 - $24

Bimbo Bakeries USA

Bimbo Bakeries USA Needs Bakery Product Delivery Driver-Independent

Chesapeake, VA

$20 - $28

Cintas

Chesapeake Job:Uniform And Linen Service Delivery Driver(Full-time)

Chesapeake, VA

$24 - $30

Cintas

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

Chesapeake, VA

$24 - $31

Pella Windows and Doors

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

Chesapeake, VA

$21 - $27

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 90+ 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 90+ open routes above and apply directly.

Last updated: October 28, 2026