Driving Jobs in Chesapeake, VA — Hiring Now

As of May 2026, there are 180+ open driving positions in Chesapeake, VA. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Chesapeake, VA

$4,480 - $7,840

FedEx

Flexible Delivery Driver in Chesapeake,VA | Hiring

Chesapeake, VA

$3,220 - $5,980

Uber

Chesapeake Contractor Role:Night Shift Ubereats Courier

Chesapeake, VA

$2,940 - $5,040

Instacart

Weekend Instacart Shopper

Chesapeake, VA

$2,200 - $3,850

Grubhub

Part-Time Delivery Driver – Chesapeake VA | Part Time Job

Chesapeake, VA

$2,500 - $4,500

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Chesapeake, VA

$2,400 - $4,200

Uber

Ubereats Large Order Delivery Driver•Chesapeake,VA•Uber | Hiring

Chesapeake, VA

$3,500 - $6,000

DoorDash

DoorDash Large Order (Catering) Driver

Chesapeake, VA

$3,220 - $5,520

PepsiCo

Route Sales Delivery Driver(Contract)|Chesapeake

Chesapeake, VA

$4,500 - $7,000

United States Postal Service

Rural Carrier Associate (RCA)

Chesapeake, VA

$3,400 - $4,800

Secure Document Couriers

Immediate Opening in Chesapeake for a Independent Contractor

Chesapeake, VA

$2,800 - $5,000

Grubhub

Part-Time Role in Chesapeake:Part-time Driver(lunch Rush) | Part

Chesapeake, VA

$800 - $1,800

Driving Jobs in Chesapeake — FAQ

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

Last updated: May 04, 2026