Updated May 2026
Best Owner-Operator Companies in Kenosha, Wisconsin (May 2026)
There are 636 owner-operator carriers currently posting jobs in Kenosha, Wisconsin. The ranking below reflects active jobs as of May 2026, not historical pay surveys. 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.
Kenosha, Wisconsin vs Wisconsin: the numbers that diverge
| Kenosha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,620 | $5,399 | +23% |
| Riders-allowed policies | 84% | 79% | +5 pt |
Source: Lanefinder index, May 2026
Among the figures above, average weekly pay is where Kenosha, Wisconsin differs most from Wisconsin — 23% above statewide.
The owner-operator carriers leading Kenosha, Wisconsin this month
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 tops the Kenosha, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC tracks as a responsive employer on application-response data. AD EXPRESS TRUCKING LLC runs a guaranteed-pay structure on the comp package.
For guaranteed weekly pay, AD EXPRESS TRUCKING LLC is the only top-10 Kenosha, Wisconsin carrier offering it.
#3D-LINE TRUCKING INC — $5,750/wk
D-LINE TRUCKING INC tracks as a responsive employer on application-response data.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 Zmile Inc at $2,175/wk, #6 TAZ TRUCKING INC at $10,999/wk, #7 SWEET EXPRESS LLC at $8,500/wk, #8 INLAND EMPIRE LLC at $7,875/wk, #9 POPE TRANSPORT INC at $7,000/wk, #10 BLUE LIGHTNING LOGISTICS at $7,000/wk.
Lane mix and benefits across Kenosha, Wisconsin
Of active CDL postings in Kenosha, Wisconsin this month, 9% are regional and 88% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
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 70%.
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 May 2026.