2026 Transportation Entry-level Jobs in Chesapeake, VA
Looking for Chesapeake entry-level jobs? Virginia’s third-biggest city is a key player in the massive center for East Coast commerce and culture known as Hampton Roads, and was named the 21st best city in America by Bloomberg Businessweek in 2011. Despite its economically powerful and visually stunning location, Chesapeake is known for its focus on protected farmlands, forests, and wetlands as opposed to sky-scraping urban centers. To highlight this emphasis on gorgeous East Coast nature, some points of interest in the city include the Chesapeake Arboretum, the Chesapeake and Albemarle Canal, and the misleadingly named Dismal Swamp Canal. But don’t let the lack of downtown high-rises fool you; Chesapeake entry-level jobs will offer you a wealth of experience and knowledge by putting you among the ranks of top-tier companies in several different fields. Some of the top employers in Chesapeake include QVC, HSBC Finance, Cox Communications, and Hewlett-Packard. For entry-level job seekers interested in the healthcare industry, there’s the Chesapeake Regional Medical Center, Sentara Healthcare, and LTD Hospitality Group to choose from. Interns looking to work in media, transportation, or government might also find Chesapeake to be ripe with worthwhile opportunities. Take a look at our list of Chesapeake entry-level jobs below and start taking your next steps towards invaluable work experience today.
Transportation Support Coordinator (Remote) — $865–$1,195 per week
Tool Room Technician
OWNER-OPERATOR DRIVERS – ALL TRAILER TYPES (1099 Independent Contractor)
OWNER-OPERATOR DRIVERS – ALL TRAILER TYPES (1099 Independent Contractor)
DOLLAR TREE LANE OPEN FOR CDL-A DRIVERS EXPERIENCED AND RECENT GRADS
Branch Engineer
Skilled Laborer
Caregiver / PCA / CNA
Direct Support Professional DSP DD waiver
Direct Support Professional (DSP) – Day Support Program
No Touch | CDL-A Truck Driver | Dry Van
# 2646 Associate Systems Engineer (SE20) -Virginia Beach, VA
Real Estate Sales Buyer's Agent
$135,000 per year
PART-TIME Registered Behavior Technician
Heavy Equipment Operator-Pipe
Looking for Field Sales Agent (ACP PROGRAM)
Sales Management Trainee
Armorer (OBMLS Specialist II)
Property Management Professional
$60,000-$70,000 per year









