Updated May 2026
Best Trucking Companies in Wisconsin (May 2026)
For W2 company drivers in Wisconsin, Lanefinder tracks 625 carriers as of May 2026. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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 trucking carriers right now
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC leads the Wisconsin market on combined pay and ranking score this month. The carrier ranks in the 96th percentile for weekly pay in Wisconsin. Strongest FMCSA dimension is controlled-substances compliance — 88th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 98th percentile across Wisconsin. Strongest FMCSA dimension is unsafe-driving avoidance — 99th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
Despite ranking below #1, True Transport Inc. outpays the leader on weekly average — $2,250/week.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's top FMCSA dimension is hours-of-service compliance, in the 94th percentile.
Covenant Transport Inc offers the highest sign-on bonus among Wisconsin's top 10 — $2,500.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 Great Plains Trucking Inc. at $1,750/wk, #6 OMAHA TRACK INC at $2,000/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 PREMIER TRANSPORTATION at $1,700/wk, #9 DIVINE ENTERPRISES at $1,375/wk, #10 CUSTOM COMMODITIES TRANSPORT at $1,750/wk.
What Wisconsin drivers actually run
The route mix in Wisconsin this month tilts OTR: 24% regional, 58% OTR, 16% local, 3% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 1% of Wisconsin postings; dedicated routes at 27%; take-truck-home at 67%. Pet-friendly policies appear at 55% and riders-allowed at 56%.
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 owner-operator companies in Wisconsin
- CDL driver salary in Wisconsin
- Best trucking companies in the United States
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 May 2026.