Updated July 2026
Best Owner-Operator Companies in Billings, Montana (July 2026)
In Billings, Montana as of July 2026, 438 carriers are actively hiring owner-operators. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. INLAND EMPIRE LLC follows at $7,875/week gross. Billings is Montana's largest city and primary freight hub on I-90 / I-94 in the Yellowstone River valley, with Bakken oil-field service loads, agricultural shipments of wheat and cattle, and regional distribution for eastern Montana.
What changed in July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Billings, Montana's top owner-operator carriers right now
The top of the list is ROLLING ON WHEELS LLC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $8,500/wk
ROLLING ON WHEELS LLC tops the Billings, Montana ranking with the strongest composite score across pay, safety, benefits, and operational signals. ROLLING ON WHEELS LLC pays above the 88th percentile on gross weekly revenue for the Billings, Montana market. On driver fitness, the carrier ranks in the 96th percentile per FMCSA SAFER data. Lanefinder's application data flags ROLLING ON WHEELS LLC as a responsive employer.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 82nd percentile on gross weekly revenue for the Billings, Montana market.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Driver applications get a faster-than-median response in Billings, Montana.
Also in the top 10: #4 Rickman Transport, LLC at $9,250/wk, #5 GNS TRUCKING INC at $9,000/wk, #6 OVERLOG INC at $3,613/wk, #7 Ali Star Inc at $10,000/wk, #8 BB8 FREIGHT CO at $12,666/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
What Billings, Montana drivers actually run
Of active CDL postings in Billings, Montana this month, 6% are regional and 93% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 2% of Billings, Montana postings; dedicated routes at 26%; take-truck-home at 93%. Pet-friendly policies appear at 75% and riders-allowed at 73%.
How Billings, Montana compares to Montana
The largest gap is on average weekly pay: Billings, Montana sits 9% above the Montana baseline.
Driving CDL in Montana
Montana freight runs the Northern Tier I-90 / I-94 corridors — long, lightly-trafficked, often beautiful, and operationally serious. Wheat and cattle freight dominate outbound; coal from the Powder River Basin generates significant rail-to-truck transfers. Oil-field service in the eastern Bakken corner of the state adds energy-sector loads. Winter is severe and long. Cost of living is moderate, with the Bozeman and Missoula corridors notably more expensive than the rest of the state. Montana has a moderate graduated state income tax. Distances are real: "long-haul" here means a different scale than the Northeast.
Related guides
- Best trucking companies in Billings, Montana
- CDL driver salary in Billings, Montana
- Best owner-operator companies in Montana
The methodology behind the rankings
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.