Updated May 2026
Best Trucking Companies in La Crosse, Wisconsin (May 2026)
La Crosse, Wisconsin has 329 active W2 trucking carriers as of May 2026. The carriers ranked below are scored on real driver pay, FMCSA safety, benefits, and how they treat applicants. 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.
Where CDL pay is strongest in La Crosse, 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 tops the La Crosse, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. KEEP TRUCKING LLC sits in the 95th percentile for weekly pay among La Crosse, Wisconsin carriers. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. Driver applications get a faster-than-median response in La Crosse, Wisconsin.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across La Crosse, Wisconsin. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 99th percentile. Driver applications get a faster-than-median response in La Crosse, Wisconsin.
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 sits in the 95th percentile for weekly pay among La Crosse, Wisconsin carriers. JK MOVING & STORAGE INC ranks in the 94th percentile for unsafe-driving avoidance on FMCSA SAFER data.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 HMD TRUCKING INC at $1,800/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 PREMIER TRANSPORTATION at $1,700/wk, #8 KEN GRAHAM TRUCKING INC at $2,000/wk, #9 KOTTKE TRUCKING INC at $2,000/wk, #10 JS HELWIG & SON LLC at $1,850/wk.
Lane mix and benefits across La Crosse, Wisconsin
Of active CDL postings in La Crosse, Wisconsin this month, 17% are regional and 81% are OTR (long-haul). Local and semi-local routes account for the remaining 2%.
Across La Crosse, Wisconsin CDL postings: 2% with guaranteed pay, 24% dedicated, 83% take-truck-home, 69% pet-friendly, 69% riders-allowed.
La Crosse, Wisconsin vs Wisconsin: the numbers that diverge
| La Crosse, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Pet-friendly fleets | 76% | 67% | +9 pt |
| Riders-allowed policies | 80% | 73% | +7 pt |
Source: Lanefinder index, May 2026
La Crosse, Wisconsin's biggest divergence from Wisconsin is on pet-friendly fleets, 9 points above the state baseline.
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 La Crosse, Wisconsin
- CDL driver salary in La Crosse, Wisconsin
- Best trucking companies in Wisconsin
The methodology behind the rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated May 2026.