Updated May 2026
Best Trucking Companies in Brookfield, Wisconsin (May 2026)
365 W2 trucking carriers are currently posting jobs in Brookfield, Wisconsin as of 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.
Where CDL pay is strongest in Brookfield, 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 Brookfield, 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 Brookfield, Wisconsin carriers. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Brookfield, Wisconsin.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Brookfield, 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 Brookfield, 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 Brookfield, Wisconsin carriers. 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 KEN GRAHAM TRUCKING INC at $2,000/wk, #8 Badger Express LLC at $1,700/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
Lane mix and benefits across Brookfield, Wisconsin
Of active CDL postings in Brookfield, Wisconsin this month, 20% are regional and 73% are OTR (long-haul). Local and semi-local routes account for the remaining 7%.
Across Brookfield, Wisconsin CDL postings: 1% with guaranteed pay, 24% dedicated, 79% take-truck-home, 64% pet-friendly, 65% riders-allowed.
How Brookfield, Wisconsin compares to Wisconsin
| Brookfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 50% | 38% | +12 pt |
| Pet-friendly fleets | 72% | 67% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on sign-on bonus availability: Brookfield, Wisconsin sits 12 points above the Wisconsin 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 Brookfield, Wisconsin
- CDL driver salary in Brookfield, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
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.