Driving Jobs in Chesapeake, VA — Now Hiring

As of May 2026, there are 160+ open driving positions in Chesapeake, VA. Current pay ranges from $12 to $393,120 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Postmates

Same-day Delivery Driver Position in Chesapeake | Hiring

Chesapeake, VA

$2,816 - $4,752

Costco Wholesale

Driver Opportunity needed in Chesapeake(Apply Now)

Chesapeake, VA

$22 - $28

Bob's Discount Furniture

Furniture Delivery Driver and Installer

Chesapeake, VA

$18 - $25

First Student

First Student seeks School Bus Driver-CDL B With Passenger And S

Chesapeake, VA

$18 - $25

Empire Auto Parts

Auto Parts Delivery Driver

Chesapeake, VA

$15 - $20

CRST The Transportation Solution

CDL A Truck Driver - OTR Team Driver

Chesapeake, VA

$79,580 - $101,200

Cersosimo Lumber Company

Chesapeake Needs:Driver Opportunity(Part-Time)

Chesapeake, VA

$28 - $36

Granite Construction

Chesapeake Job:CDL B Water Truck Driver-Construction Site Dust Control

Chesapeake, VA

$27 - $33

Old Dominion Freight Line

[Part-Time] Driver Opportunity-Chesapeake

Chesapeake, VA

$80,000 - $95,000

General Beer Northeast

Chesapeake Part-Time Job:Beer Delivery Driver-CDL A Distributor

Chesapeake, VA

$25 - $32

Amazon Flex

Amazon Flex is hiring a Holiday Peak Delivery Driver in Chesapeake

Chesapeake, VA

$4,140 - $6,900

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Chesapeake, VA

$2,800 - $5,000

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 160+ open driving positions in Chesapeake, VA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Chesapeake?
Driving job pay in Chesapeake varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Chesapeake?
Yes. Many delivery driver, courier, and DSP positions in Chesapeake require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Chesapeake?
Driving jobs in Chesapeake offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Chesapeake?
Benefits vary by employer, but many driving positions in Chesapeake offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Chesapeake?
Your take-home pay as a driver in Chesapeake depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Chesapeake?
Yes, many driving positions in Chesapeake are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 160+ listings above and apply directly.

Last updated: May 13, 2026