Updated September 2026
Best Owner-Operator Companies in Chesapeake, Virginia (September 2026)
573 carriers are hiring owner-operators in Chesapeake, Virginia right now, per Lanefinder's September 2026 snapshot. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. 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 Chesapeake, Virginia differs from the Virginia baseline
| Chesapeake, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,287 | $5,276 | +19% |
| Sign-on bonus rate | 24% | 29% | -5 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Chesapeake, Virginia sits 19% above the Virginia baseline.
Where owner-operator pay is strongest in Chesapeake, Virginia this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC is number-one in Chesapeake, Virginia this month on the composite ranking. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 94th percentile across Chesapeake, Virginia. Top FMCSA dimension here is driver fitness, in the 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Chesapeake, Virginia median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Driver applications get a faster-than-median response in Chesapeake, Virginia.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 WIDER GROUP INC at $6,250/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 KILO METER LOGISTIC INC at $7,500/wk, #8 C & G TRANSPORTATION INC at $7,500/wk, #9 M&D TRANSPORT at $7,000/wk, #10 AIA TRUCKING INC at $3,450/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 9% are regional and 90% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 2% of Chesapeake, Virginia postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 72% and riders-allowed at 71%.
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 trucking companies in Chesapeake, Virginia
- CDL driver salary in Chesapeake, Virginia
- Best owner-operator companies in Virginia
Where this data comes from
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated September 2026.