Updated May 2026
Best Trucking Companies in Milwaukee, Wisconsin (May 2026)
Lanefinder is tracking 361 W2 trucking carriers in Milwaukee, Wisconsin (May 2026). KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Milwaukee anchors I-94 on Lake Michigan with a port handling dry bulk and breakbulk cargo, with a dense manufacturing base in industrial goods and packaging, and Midwest distribution via I-94 and I-43.
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 Milwaukee, 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 Milwaukee, Wisconsin market on combined pay and ranking score this month. Weekly pay here lands in the 95th percentile across Milwaukee, Wisconsin. Top FMCSA dimension here is controlled-substances compliance, in the 88th percentile. KEEP TRUCKING LLC tracks as a responsive employer on application-response data.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 92nd percentile on weekly pay for the Milwaukee, Wisconsin market. Top FMCSA dimension here is unsafe-driving avoidance, in the 99th percentile. Application-response data flags this carrier as a responsive employer.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC sits in the 95th percentile for weekly pay among Milwaukee, Wisconsin carriers. On unsafe-driving avoidance, the carrier ranks in the 94th percentile per 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 Milwaukee, Wisconsin drivers actually run
Of active CDL postings in Milwaukee, Wisconsin this month, 20% are regional and 73% are OTR (long-haul). Local and semi-local routes account for the remaining 7%.
Guaranteed pay is on offer at 1% of Milwaukee, Wisconsin postings; dedicated routes at 24%; take-truck-home at 79%. Pet-friendly policies appear at 64% and riders-allowed at 65%.
Where Milwaukee, Wisconsin differs from the Wisconsin baseline
| Milwaukee, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 46% | 38% | +8 pt |
| Pet-friendly fleets | 72% | 67% | +5 pt |
Source: Lanefinder index, May 2026
Among the figures above, sign-on bonus availability is where Milwaukee, Wisconsin differs most from Wisconsin — 8 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 Milwaukee, Wisconsin
- CDL driver salary in Milwaukee, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
Carriers are scored against carriers in their own market. The composite is 30% compensation (pay + bonus + guaranteed pay + settlement cadence), 25% FMCSA safety, 25% benefits (W2 vs owner-op scoring), and 20% operational performance (responsiveness + fleet scale). No paid placement — the weights are the same for every carrier in the index. Updated May 2026.