Updated July 2026
Best Owner-Operator Companies in Kenosha, Wisconsin (July 2026)
There are 632 owner-operator carriers currently posting jobs in Kenosha, Wisconsin. The ranking below reflects active jobs as of July 2026, not historical pay surveys. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. WINNERS TRANSPORTATION LLC follows at $2,437/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 July 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 ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC tops the Kenosha, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Kenosha, Wisconsin median.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Kenosha, Wisconsin median.
#3TITANIUM AMERICAN TRUCKING INC — $6,250/wk
TITANIUM AMERICAN TRUCKING INC's top FMCSA dimension is hours-of-service compliance, in the 97th percentile.
Also in the top 10: #4 SWEET EXPRESS LLC at $8,500/wk, #5 WIDER GROUP INC at $6,250/wk, #6 OVERLOG INC at $3,145/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BB8 FREIGHT CO at $12,666/wk, #10 DAHL TRUCKING LLC at $3,750/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 27%; take-truck-home at 92%. Pet-friendly policies appear at 74% and riders-allowed at 69%.
Kenosha, Wisconsin vs Wisconsin: the numbers that diverge
| Kenosha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,016 | $5,352 | +12% |
| Riders-allowed policies | 84% | 78% | +6 pt |
Source: Lanefinder index, July 2026
Among the figures above, average weekly pay is where Kenosha, Wisconsin differs most from Wisconsin — 12% 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 July 2026.