Driving Jobs in Chesapeake, VA — See Openings

As of April 2026, there are 140+ open driving positions in Chesapeake, VA. Current pay ranges from $500 to $8,500 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Part-Time Job in Chesapeake:Night Shift Courier | Part Time Job

Chesapeake, VA

$2,800 - $4,800

Shipt

[Part-Time] Evening & Night Shift Courier-Chesapeake

Chesapeake, VA

$2,800 - $4,800

Grubhub

Flexible Part-Time Early Morning Driver in Chesapeake | Part Time

Chesapeake, VA

$2,200 - $3,800

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Chesapeake, VA

$4,550 - $7,735

Instacart

Suburban Instacart Shopper

Chesapeake, VA

$2,464 - $4,224

DoorDash

DoorDash Shop & Deliver Expert (Grocery/Retail)

Chesapeake, VA

$2,800 - $4,800

DoorDash

Part-Time DoorDash Driver (Lunch Rush Specialist)

Chesapeake, VA

$800 - $1,800

Shipt

(Chesapeake)Part-Time:Courier

Chesapeake, VA

$2,000 - $3,500

Uber

Flexible Ubereats Large Order Delivery Driver(Chesapeake)

Chesapeake, VA

$3,500 - $6,000

On-Demand Tasks Network

Chesapeake:Independent Contractor Driver-On-demand Errands

Chesapeake, VA

$2,200 - $4,400

Grubhub

Grubhub Shop and Pay Driver

Chesapeake, VA

$2,800 - $4,800

Grubhub

Suburban Route Grubhub Driver

Chesapeake, VA

$2,760 - $4,830

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 140+ 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 140+ listings above and apply directly.

Last updated: April 26, 2026