Updated May 2026
Best Trucking Companies in Kenosha, Wisconsin (May 2026)
390 W2 trucking carriers are hiring in Kenosha, Wisconsin this 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.
The trucking companies leading Kenosha, Wisconsin this month
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 Kenosha, Wisconsin market on combined pay and ranking score this month. Pay sits above the 90th percentile in the Kenosha, Wisconsin market. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. KEEP TRUCKING LLC responds to driver applications more reliably than the Kenosha, Wisconsin median.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Kenosha, Wisconsin. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 99th percentile. True Transport Inc. responds to driver applications more reliably than the Kenosha, Wisconsin median.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC's weekly pay ranks in the 95th percentile across Kenosha, Wisconsin. Strongest FMCSA dimension is unsafe-driving avoidance — 94th percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 PREMIER TRANSPORTATION at $1,700/wk, #7 Badger Express LLC at $1,700/wk, #8 DIVINE ENTERPRISES at $1,375/wk, #9 KEN GRAHAM TRUCKING INC at $2,000/wk, #10 JS HELWIG & SON LLC at $1,850/wk.
Lane mix and benefits across Kenosha, Wisconsin
19% of Kenosha, Wisconsin's active CDL postings are regional and 68% are OTR; local plus semi-local accounts for the rest (13%).
Across Kenosha, Wisconsin CDL postings: 1% with guaranteed pay, 26% dedicated, 74% take-truck-home, 61% pet-friendly, 61% riders-allowed.
How Kenosha, Wisconsin compares to Wisconsin
| Kenosha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 44% | 38% | +6 pt |
| Take-truck-home | 84% | 90% | -6 pt |
Source: Lanefinder index, May 2026
Among the figures above, sign-on bonus availability is where Kenosha, Wisconsin differs most from Wisconsin — 6 points 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 owner-operator companies in Kenosha, Wisconsin
- CDL driver salary in Kenosha, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
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.