Updated September 2026
Best Owner-Operator Companies in La Crosse, Wisconsin (September 2026)
For owner-operators in La Crosse, Wisconsin, Lanefinder tracks 591 carriers as of September 2026. 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. Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison, with dairy and food processing as the dominant outbound commodity and paper and packaging manufacturing in the Fox River Valley generating consistent industrial loads.
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 La Crosse, Wisconsin differs from the Wisconsin baseline
| La Crosse, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,684 | $5,277 | +27% |
| Riders-allowed policies | 90% | 80% | +10 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where La Crosse, Wisconsin differs most from Wisconsin — 27% above statewide.
Where owner-operator pay is strongest in La Crosse, Wisconsin 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 leads the La Crosse, Wisconsin market on combined gross revenue and ranking score this month. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 94th percentile across La Crosse, Wisconsin. 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 La Crosse, Wisconsin 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 La Crosse, Wisconsin.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 WIDER GROUP INC at $6,250/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 Ali Star Inc at $10,000/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 AIA TRUCKING INC at $3,450/wk.
Lane mix and benefits across La Crosse, Wisconsin
7% of La Crosse, Wisconsin's active CDL postings are regional and 93% are OTR; local plus semi-local accounts for the rest (0%).
Guaranteed pay is on offer at 2% of La Crosse, Wisconsin postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 74% and riders-allowed at 71%.
Driving CDL in Wisconsin
Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison. Dairy and food processing are dominant outbound commodities — Wisconsin's reefer freight is a national-scale segment. Paper and packaging manufacturing in the Fox River Valley generates consistent industrial loads. Great Lakes ports at Green Bay and Superior handle bulk cargo. Cost of living is moderate. Wisconsin has a high graduated state income tax. Winter is severe — lake-effect snow off Lake Michigan affects the eastern third of the state; ice and salt corrosion eat equipment faster than southern states.
Related guides
- Best trucking companies in La Crosse, Wisconsin
- CDL driver salary in La Crosse, Wisconsin
- Best owner-operator companies in Wisconsin
Where this data comes from
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated September 2026.