Updated September 2026
Best Owner-Operator Companies in Kenosha, Wisconsin (September 2026)
There are 636 owner-operator carriers currently posting jobs in Kenosha, Wisconsin. The ranking below reflects active jobs as of September 2026, not historical pay surveys. 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.
The owner-operator carriers leading Kenosha, 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 tops the Kenosha, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 95th percentile for gross weekly revenue in Kenosha, 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 Kenosha, 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 Kenosha, 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 SWEET EXPRESS LLC at $8,500/wk, #7 WIDER GROUP INC at $6,250/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
Lane mix and benefits across Kenosha, Wisconsin
Of active CDL postings in Kenosha, Wisconsin this month, 9% are regional and 89% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Guaranteed pay is on offer at 2% of Kenosha, Wisconsin postings; dedicated routes at 28%; take-truck-home at 92%. Pet-friendly policies appear at 73% and riders-allowed at 69%.
Kenosha, Wisconsin vs Wisconsin: the numbers that diverge
Among the figures above, average weekly pay is where Kenosha, Wisconsin differs most from Wisconsin — 14% above statewide.
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 Kenosha, Wisconsin
- CDL driver salary in Kenosha, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
Composite-score formula: compensation × 0.30, FMCSA safety × 0.25, benefits × 0.25, operational performance × 0.20. Compensation is anchored on pay percentile and lifted by sign-on bonus tier and guaranteed-pay availability. Operational performance is built mostly from driver-application response data in Lanefinder's platform, with fleet-scale percentile contributing a smaller portion. Updated September 2026.