Driving Jobs in Chesapeake, VA — Open Positions

As of April 2026, there are 230+ open driving positions in Chesapeake, VA. Current pay ranges from $460 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.

Shipt

Hiring in Chesapeake:Midday Shopper(Part-Time)

Chesapeake, VA

$1,000 - $2,000

Amazon AMXL Delivery Partners

Amazon AMXL Box Truck Delivery Driver

Chesapeake, VA

$4,410 - $6,090

Morning Express Couriers

Driver Opportunity(Part-Time)@ Morning Express Couriers-Chesapeake

Chesapeake, VA

$2,090 - $3,610

Instacart

Weekend Instacart Shopper

Chesapeake, VA

$2,000 - $3,500

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Chesapeake, VA

$5,400 - $9,180

Uber

$3k-$5.5k/Month EV Rideshare Driver job in Chesapeake | Hiring

Chesapeake, VA

$3,000 - $5,500

Fresh Crust Logistics

Driver Opportunity(Part-Time)@ Fresh Crust Logistics-Chesapeake

Chesapeake, VA

$3,500 - $5,000

Heavy Haul Last Mile

Part-Time Job in Chesapeake:Heavy/bulky Item Delivery Specialist

Chesapeake, VA

$3,800 - $5,500

FedEx Ground Independent Contractor

Earn Extra Cash:Driver Opportunity(Chesapeake)

Chesapeake, VA

$4,200 - $6,300

United Parcel Service (UPS)

Chesapeake Job:Driver Opportunity(No Exp Req*)

Chesapeake, VA

$4,275 - $7,600

United States Postal Service

Commercial Box Truck Mail Courier (MVO)

Chesapeake, VA

$3,400 - $5,100

Corporate Catering Couriers

Corporate Catering Couriers Needs Independent Contractor

Chesapeake, VA

$3,500 - $6,000

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 230+ 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 230+ listings above and apply directly.

Last updated: April 17, 2026