Updated July 2026
Best Trucking Companies in Chesapeake, Virginia (July 2026)
269 W2 trucking carriers are hiring in Chesapeake, Virginia this July 2026. True Transport Inc. leads with an average weekly pay of $2,250. CARGORX DRY CAPACITY follows at $1,900/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 July 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 True Transport Inc. at $2,250/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1True Transport Inc. — $2,250/wk
True Transport Inc. leads the Chesapeake, Virginia market on combined pay and ranking score this month. True Transport Inc. sits in the 95th 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.
#2CARGORX DRY CAPACITY — $1,900/wk
CARGORX DRY CAPACITY's top FMCSA dimension is hours-of-service compliance, in the 89th percentile. CARGORX DRY CAPACITY responds to driver applications more reliably than the Chesapeake, Virginia median.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC's weekly pay ranks in the 93rd percentile across Chesapeake, Virginia. Strongest FMCSA dimension is unsafe-driving avoidance — 93rd percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 ECM ENERGY SERVICES INC at $1,950/wk, #7 Diaz Stone & Pallet Inc. at $1,750/wk, #8 JS HELWIG & SON LLC at $1,850/wk, #9 CUSTOM TRANSPORT INC at $2,500/wk, #10 G & C FOOD DISTRIBUTORS & BROKERS INC at $1,650/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 18% are regional and 79% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Chesapeake, Virginia CDL postings: 2% with guaranteed pay, 25% dedicated, 81% take-truck-home, 68% pet-friendly, 66% riders-allowed.
Chesapeake, Virginia vs Virginia: the numbers that diverge
| Chesapeake, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Riders-allowed policies | 84% | 73% | +11 pt |
| Dedicated routes | 26% | 33% | -7 pt |
Source: Lanefinder index, July 2026
The largest gap is on riders-allowed policies: Chesapeake, Virginia sits 11 points above 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 July 2026.