Updated July 2026
Best Trucking Companies in Milwaukee, Wisconsin (July 2026)
Lanefinder is tracking 352 W2 trucking carriers in Milwaukee, Wisconsin (July 2026). LAWRENCE TRANSPORTATION COMPANY leads with an average weekly pay of $1,680. Forest Brook Trucking LLC follows at $1,600/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 July 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 LAWRENCE TRANSPORTATION COMPANY at $1,680/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1LAWRENCE TRANSPORTATION COMPANY — $1,680/wk
LAWRENCE TRANSPORTATION COMPANY tops the Milwaukee, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. LAWRENCE TRANSPORTATION COMPANY ranks in the 91st percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2Forest Brook Trucking LLC — $1,600/wk
Forest Brook Trucking LLC's FMCSA score is strongest on hours-of-service compliance — 97th percentile. Application-response data flags this carrier as a responsive employer.
#3True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 91st percentile on weekly pay for the Milwaukee, Wisconsin market. Top FMCSA dimension here is unsafe-driving avoidance, in the 99th percentile.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
Also in the top 10: #4 PREMIER TRANSPORTATION at $1,950/wk, #5 JK MOVING & STORAGE INC at $2,200/wk, #6 Covenant Transport Inc at $1,762/wk, #7 South East Carriers INC at $1,600/wk, #8 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #9 Diaz Stone & Pallet Inc. at $1,750/wk, #10 Badger Express LLC at $1,700/wk.
What Milwaukee, Wisconsin drivers actually run
Of active CDL postings in Milwaukee, Wisconsin this month, 20% are regional and 72% are OTR (long-haul). Local and semi-local routes account for the remaining 8%.
Guaranteed pay is on offer at 2% of Milwaukee, Wisconsin postings; dedicated routes at 24%; take-truck-home at 78%. Pet-friendly policies appear at 63% and riders-allowed at 64%.
Where Milwaukee, Wisconsin differs from the Wisconsin baseline
Among the figures above, sign-on bonus availability is where Milwaukee, Wisconsin differs most from Wisconsin — 13 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 July 2026.