Updated September 2026
Best Trucking Companies in Chesapeake, Virginia (September 2026)
269 W2 trucking carriers are hiring in Chesapeake, Virginia this September 2026. JK MOVING & STORAGE INC leads with an average weekly pay of $2,200. Big Foot Transport LLC follows at $2,650/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 September 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 JK MOVING & STORAGE INC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC tops the Chesapeake, Virginia ranking with the strongest composite score across pay, safety, benefits, and operational signals. JK MOVING & STORAGE INC's weekly pay ranks in the 93rd percentile across Chesapeake, Virginia. Strongest FMCSA dimension is unsafe-driving avoidance — 93rd percentile.
#2Big Foot Transport LLC — $2,650/wk
Big Foot Transport LLC pays above the 94th percentile on weekly pay for the Chesapeake, Virginia market. Big Foot Transport LLC ranks in the 88th percentile on FMCSA's composite safety percentile. Big Foot Transport LLC tracks as a responsive employer on application-response data.
For pure pay maximization, Big Foot Transport LLC beats the #1-ranked carrier weekly at $2,650.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc ranks in the 99th percentile for driver fitness on FMCSA SAFER data.
Also in the top 10: #4 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #5 ECM ENERGY SERVICES INC at $1,950/wk, #6 HandledNow LLC at $1,800/wk, #7 True Transport Inc. at $2,250/wk, #8 JS HELWIG & SON LLC at $1,850/wk, #9 Diaz Stone & Pallet Inc. at $1,750/wk, #10 G-DIAMOND TRANSPORT INC at $2,045/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 19% are regional and 79% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Across Chesapeake, Virginia CDL postings: 2% with guaranteed pay, 25% dedicated, 82% take-truck-home, 69% pet-friendly, 66% riders-allowed.
Chesapeake, Virginia vs Virginia: the numbers that diverge
| Chesapeake, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Pet-friendly fleets | 76% | 66% | +10 pt |
| Riders-allowed policies | 84% | 74% | +10 pt |
| Dedicated routes | 26% | 34% | -8 pt |
Source: Lanefinder index, September 2026
The largest gap is on pet-friendly fleets: Chesapeake, Virginia sits 10 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 September 2026.