Updated May 2026
Best Owner-Operator Companies in Wisconsin (May 2026)
Lanefinder tracks 718 owner-operator carriers hiring in Wisconsin. Rankings below reflect May 2026 data: pay percentiles, FMCSA safety, benefit prevalence, and operational performance. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. AD EXPRESS TRUCKING LLC follows at $2,600/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 May 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 YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC is number-one in Wisconsin this month on the composite ranking. YANKEE FREIGHT SYSTEMS LLC's FMCSA score is strongest on hours-of-service compliance — 98th percentile. Driver applications get a faster-than-median response in Wisconsin.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
Lanefinder's application data flags AD EXPRESS TRUCKING LLC as a responsive employer. AD EXPRESS TRUCKING LLC guarantees weekly pay — useful when freight slows down.
AD EXPRESS TRUCKING LLC stands alone in Wisconsin's top 10 on guaranteed pay — every other ranked carrier here pays per-mile or per-load.
#3D-LINE TRUCKING INC — $5,750/wk
Lanefinder's application data flags D-LINE TRUCKING INC as a responsive employer.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 INLAND EMPIRE LLC at $7,875/wk, #7 POPE TRANSPORT INC at $7,000/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 M&D TRANSPORT at $7,000/wk, #10 Red Diamond Freight, LLC at $6,750/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, 28% dedicated, 92% take-truck-home, 73% pet-friendly, 68% 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 May 2026.