Updated September 2026
Best Owner-Operator Companies in Wisconsin (September 2026)
Lanefinder tracks 720 owner-operator carriers hiring in Wisconsin. Rankings below reflect September 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. 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.
Wisconsin's top owner-operator carriers right now
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 Wisconsin this month on the composite ranking. RAY'S TRANSPORT INC sits in the 96th percentile for gross weekly revenue among Wisconsin carriers. RAY'S TRANSPORT INC's top FMCSA dimension is driver fitness, in the 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Wisconsin median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 WIDER GROUP INC at $6,250/wk, #7 POPE TRANSPORT INC at $7,000/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 AIA TRUCKING INC at $3,450/wk, #10 M&D TRANSPORT at $7,000/wk.
How drivers spend their time on the road in Wisconsin
Of active CDL postings in Wisconsin this month, 12% are regional and 85% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Wisconsin CDL postings: 2% with guaranteed pay, 29% dedicated, 91% take-truck-home, 71% pet-friendly, 67% riders-allowed.
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 Wisconsin
- CDL driver salary in Wisconsin
- Best owner-operator companies in the United States
The methodology behind the rankings
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated September 2026.