Driving Jobs in Chesapeake, VA — See Openings

As of October 2026, there are 250+ open driving positions in Chesapeake, VA. Current pay ranges from $12 to $364,000 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.

Amazon Flex

Amazon Flex Needs Delivery Driver-Independent Contractor in Chesapeake

Chesapeake, VA

$18 - $25

Medline Industries

Chesapeake Part-Time:Medline Medical Supply Delivery Driver

Chesapeake, VA

$24 - $31

PepsiCo

Beverage Distribution Box Truck Driver(Contract)-Chesapeake,VA

Chesapeake, VA

$5,000 - $7,500

LKQ Corporation

Flexible Part-Time LKQ Heavy Duty Auto Parts Box Truck Driver in

Chesapeake, VA

$4,200 - $6,500

US Postal Service Contractors

Chesapeake:Highway Contract Route(HCR)Driver(Contractor,$4k-$7k/Month)

Chesapeake, VA

$4,000 - $7,000

US Auto Parts Logistics

US Auto Parts-Hybrid Warehouse & Delivery Driver|Part-Time

Chesapeake, VA

$3,200 - $4,800

Sherwin-Williams

Paint Store Delivery Driver - Commercial Accounts

Chesapeake, VA

$19 - $25

Bimbo Bakeries USA

Immediate Start:Bimbo Bakeries Box Truck Route Driver

Chesapeake, VA

$4,000 - $5,500

United Parcel Service (UPS)

UPS Commercial Box Truck Driver|Flexible|Chesapeake

Chesapeake, VA

$5,000 - $8,500

SnackRoute Solutions

Chesapeake Vending Route Step Van Driver($3.2k-$4.8k/Month) | Hiring

Chesapeake, VA

$3,200 - $4,800

United States Postal Service

USPS City Carrier Assistant

Chesapeake, VA

$2,890 - $4,080

Hunt Transportation

CDL A Truck Driver - Dedicated Account Home Daily

Chesapeake, VA

$73,500 - $99,750

Driving Jobs in Chesapeake — FAQ

How many driving jobs are available in Chesapeake, VA right now?
There are currently 250+ 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 250+ listings above and apply directly.

Last updated: October 03, 2026