Updated May 2026
Best Trucking Companies in Waukesha, Wisconsin (May 2026)
In Waukesha, Wisconsin as of May 2026, 369 carriers are actively hiring W2 company drivers. 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.
Waukesha, Wisconsin's top trucking carriers right now
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 is number-one in Waukesha, Wisconsin this month on the composite ranking. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Waukesha, Wisconsin market. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. Driver applications get a faster-than-median response in Waukesha, Wisconsin.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 92nd percentile on weekly pay for the Waukesha, Wisconsin market. On unsafe-driving avoidance, the carrier ranks in the 99th percentile per FMCSA SAFER data. Lanefinder's application data flags True Transport Inc. as a responsive employer.
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 pays above the 90th percentile on weekly pay for the Waukesha, Wisconsin market. 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 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 PREMIER TRANSPORTATION at $1,700/wk, #7 Badger Express LLC at $1,700/wk, #8 KEN GRAHAM TRUCKING INC at $2,000/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Waukesha, Wisconsin drivers actually run
21% of Waukesha, Wisconsin's active CDL postings are regional and 72% are OTR; local plus semi-local accounts for the rest (7%).
Across Waukesha, Wisconsin CDL postings: 1% with guaranteed pay, 24% dedicated, 79% take-truck-home, 64% pet-friendly, 64% riders-allowed.
Waukesha, Wisconsin vs Wisconsin: the numbers that diverge
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 48% | 38% | +10 pt |
| Pet-friendly fleets | 72% | 67% | +5 pt |
Source: Lanefinder index, May 2026
Among the figures above, sign-on bonus availability is where Waukesha, Wisconsin differs most from Wisconsin — 10 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 Waukesha, Wisconsin
- CDL driver salary in Waukesha, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
The score is built from four buckets. Thirty percent compensation, drawn from real active job postings and modified by bonus and settlement structure. Twenty-five percent safety, from FMCSA SAFER. Twenty-five percent benefits, scored hiring-type-aware. Twenty percent operational performance, drawn from how carriers actually behave toward applicants. Updated May 2026.