Updated May 2026
Best Trucking Companies in Chesapeake, Virginia (May 2026)
274 W2 trucking carriers are hiring in Chesapeake, Virginia this May 2026. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads, the deepest commercial harbor on the East Coast (55 ft after the Gateway dredging program), with I-95 / I-64 / I-81 truck corridors connecting it to the mid-Atlantic and Southeast markets.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where CDL pay is strongest in Chesapeake, Virginia this month
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC is number-one in Chesapeake, Virginia this month on the composite ranking. Pay sits above the 89th percentile in the Chesapeake, Virginia market. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. Lanefinder's application data flags KEEP TRUCKING LLC as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 96th percentile for weekly pay among Chesapeake, Virginia carriers. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. Driver applications get a faster-than-median response in Chesapeake, Virginia.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC's weekly pay ranks in the 94th percentile across Chesapeake, Virginia. Strongest FMCSA dimension is unsafe-driving avoidance — 94th percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 HMD TRUCKING INC at $1,800/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 YARBROUGH TRANSFER COMPANY at $1,850/wk, #8 ECM ENERGY SERVICES INC at $1,950/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 18% are regional and 80% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Across Chesapeake, Virginia CDL postings: 2% with guaranteed pay, 24% dedicated, 83% take-truck-home, 68% pet-friendly, 67% riders-allowed.
Chesapeake, Virginia vs Virginia: the numbers that diverge
| Chesapeake, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Dedicated routes | 26% | 35% | -9 pt |
| Riders-allowed policies | 82% | 75% | +7 pt |
| Pet-friendly fleets | 76% | 71% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on dedicated routes: Chesapeake, Virginia sits 9 points below the Virginia baseline.
Driving CDL in Virginia
Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads — the deepest commercial harbor on the East Coast and a top-tier US container gateway. The I-95 / I-64 / I-81 truck corridors connect Norfolk to mid-Atlantic and Southeast markets, with I-81 north-south through the Shenandoah Valley a major regional freight spine. Cost of living varies widely (high in Northern Virginia, moderate elsewhere). Virginia has a moderate graduated state income tax. Northern Virginia (DC suburbs) congestion is consistently top-tier; central and western VA is generally easier driving.
Related guides
- Best owner-operator companies in Chesapeake, Virginia
- CDL driver salary in Chesapeake, Virginia
- Best trucking companies in Virginia
The methodology behind the rankings
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated May 2026.