Updated September 2026
Best Owner-Operator Companies in Billings, Montana (September 2026)
In Billings, Montana as of September 2026, 439 carriers are actively hiring owner-operators. WINNERS TRANSPORTATION LLC leads with an average gross weekly revenue of $2,657 and an average $2,142 sign-on bonus. WESTERN MOUNTAIN TRANSPORT INC follows at $8,500/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 September 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 WINNERS TRANSPORTATION LLC at $2,657/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC tops the Billings, Montana ranking with the strongest composite score across pay, safety, benefits, and operational signals. WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. Driver applications get a faster-than-median response in Billings, Montana.
#2WESTERN MOUNTAIN TRANSPORT INC — $8,500/wk
WESTERN MOUNTAIN TRANSPORT INC's gross weekly revenue ranks in the 94th percentile across Billings, Montana. WESTERN MOUNTAIN TRANSPORT INC ranks in the 93rd percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#3Rickman Transport, LLC — $9,250/wk
Rickman Transport, LLC pays above the 90th percentile on gross weekly revenue for the Billings, Montana market. Rickman Transport, LLC's FMCSA score is strongest on unsafe-driving avoidance — 91st percentile.
For sign-on cash, Rickman Transport, LLC posts the largest bonus in Billings, Montana's top 10 at $6,000.
Also in the top 10: #4 Ali Star Inc at $10,000/wk, #5 GNS TRUCKING INC at $9,000/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 TITAN FREIGHT LINES INC at $8,500/wk, #10 ARCHER HOLDING GROUP at $8,000/wk.
What Billings, Montana drivers actually run
Of active CDL postings in Billings, Montana this month, 7% are regional and 93% are OTR (long-haul). Local and semi-local routes account for the remaining 0%.
Guaranteed pay is on offer at 2% of Billings, Montana postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 74% and riders-allowed at 73%.
How Billings, Montana compares to Montana
| Billings, Montana | Montana top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $7,501 | $6,980 | +7% |
| Dedicated routes | 50% | 44% | +6 pt |
Source: Lanefinder index, September 2026
The largest gap is on average weekly pay: Billings, Montana sits 7% 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 September 2026.