Updated July 2026
Best Owner-Operator Companies in Chesapeake, Virginia (July 2026)
566 carriers are hiring owner-operators in Chesapeake, Virginia right now, per Lanefinder's July 2026 snapshot. Performance Trucking Inc leads with an average gross weekly revenue of $8,000. ROLLING ON WHEELS LLC follows at $5,500/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 July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where owner-operator pay is strongest in Chesapeake, Virginia this month
The top of the list is Performance Trucking Inc at $8,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Performance Trucking Inc — $8,000/wk
Performance Trucking Inc tops the Chesapeake, Virginia ranking with the strongest composite score across pay, safety, benefits, and operational signals. Performance Trucking Inc sits in the 93rd percentile for gross weekly revenue among Chesapeake, Virginia carriers.
#2ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Driver applications get a faster-than-median response in Chesapeake, Virginia.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 85th percentile on gross weekly revenue for the Chesapeake, Virginia market.
Also in the top 10: #4 WINNERS TRANSPORTATION LLC at $2,437/wk, #5 OVERLOG INC at $3,613/wk, #6 WIDER GROUP INC at $6,250/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 C & G TRANSPORTATION INC at $7,500/wk, #9 BB8 FREIGHT CO at $12,666/wk, #10 TP TRUCKING at $8,500/wk.
What Chesapeake, Virginia drivers actually run
Of active CDL postings in Chesapeake, Virginia this month, 8% are regional and 92% are OTR (long-haul). Local and semi-local routes account for the remaining 0%.
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 73% and riders-allowed at 71%.
Where Chesapeake, Virginia differs from the Virginia baseline
The largest gap is on average weekly pay: Chesapeake, Virginia sits 14% 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 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 July 2026.