Updated November 2026
Best Trucking Companies in Milwaukee, Wisconsin (November 2026)
Lanefinder is tracking 358 W2 trucking carriers in Milwaukee, Wisconsin (November 2026). Herrington Transportation Inc. leads with an average weekly pay of $2,000. 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 November 2026
McLeod Express LLC at #3, SAFE WAY CARRIER LLC at #5, and MNS1 EXPRESS INC at #7 are new to the top 50 in Milwaukee, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#37 → #1) and True Transport Inc. (#13 → #2). Biggest fall: LAWRENCE TRANSPORTATION COMPANY (#1 → #24). Elsewhere in the top 50, 5 carriers joined, 8 left, and 36 changed rank.
All changes since October 2026
Where CDL pay is strongest in Milwaukee, Wisconsin this month
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. leads the Milwaukee, Wisconsin market on combined pay and ranking score this month. Pay sits above the 86th percentile in the Milwaukee, Wisconsin market. Lanefinder's application data flags Herrington Transportation Inc. as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. rose 11 positions month-over-month, from #13 to #2. The carrier ranks in the 97th percentile for weekly pay in Milwaukee, Wisconsin. Top FMCSA dimension here is unsafe-driving avoidance, in the 98th percentile.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
#3McLeod Express LLC — $1,483/wk
McLeod Express LLC debuts in the Milwaukee, Wisconsin top 50 this month — it wasn't tracked here last month. Top FMCSA dimension here is unsafe-driving avoidance, in the 94th percentile. McLeod Express LLC runs a guaranteed-pay structure on the comp package.
McLeod Express LLC is the lone Milwaukee, Wisconsin top-10 carrier offering OTR work with a guaranteed weekly wage.
Also in the top 10: #4 PREMIER TRANSPORTATION at $1,950/wk, #5 SAFE WAY CARRIER LLC at $2,100/wk, #6 JK MOVING & STORAGE INC at $2,200/wk, #7 MNS1 EXPRESS INC at $2,050/wk, #8 HandledNow LLC at $1,550/wk, #9 Covenant Transport Inc at $1,762/wk, #10 Mountain States L.P. Gas at $2,000/wk.
What Milwaukee, Wisconsin drivers actually run
Of active CDL postings in Milwaukee, Wisconsin this month, 21% are regional and 72% are OTR (long-haul). Local and semi-local routes account for the remaining 7%.
Guaranteed pay is on offer at 2% of Milwaukee, Wisconsin postings; dedicated routes at 25%; take-truck-home at 78%. Pet-friendly policies appear at 64% and riders-allowed at 65%.
Where Milwaukee, Wisconsin differs from the Wisconsin baseline
Among the figures above, dedicated routes is where Milwaukee, Wisconsin differs most from Wisconsin — 11 points below statewide.
Driving CDL in Milwaukee
Milwaukee anchors southeastern Wisconsin on I-94 / I-43 / I-794. Manufacturing (Harley-Davidson HQ, GE HealthCare's largest US manufacturing and engineering footprint (consolidating into the Waukesha campus; corporate HQ now in Chicago)), Northwestern Mutual HQ, and distribution serving the Lake Michigan corridor drive freight. Cost of living is moderate. Lake-effect snow off Lake Michigan affects the city in winter; salt corrosion is real.
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 November 2026.