Updated July 2026
Best Owner-Operator Companies in Milwaukee, Wisconsin (July 2026)
There are 613 owner-operator carriers currently posting jobs in Milwaukee, Wisconsin. The ranking below reflects active jobs as of July 2026, not historical pay surveys. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. WINNERS TRANSPORTATION LLC follows at $2,437/week gross. 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.
How Milwaukee, Wisconsin compares to Wisconsin
| Milwaukee, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,115 | $5,295 | +15% |
| Riders-allowed policies | 86% | 78% | +8 pt |
Source: Lanefinder index, July 2026
The largest gap is on average weekly pay: Milwaukee, Wisconsin sits 15% above the Wisconsin baseline.
Where owner-operator pay is strongest in Milwaukee, Wisconsin this month
The top of the list is ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC leads the Milwaukee, Wisconsin market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Milwaukee, Wisconsin market.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 OVERLOG INC at $3,613/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 POPE TRANSPORT INC at $7,000/wk, #10 BB8 FREIGHT CO at $12,666/wk.
What Milwaukee, Wisconsin drivers actually run
The route mix in Milwaukee, Wisconsin this month tilts OTR: 9% regional, 90% OTR, 1% local, 0% semi-local — drawn from active postings, not historical surveys.
Across Milwaukee, Wisconsin CDL postings: 2% with guaranteed pay, 27% dedicated, 92% take-truck-home, 75% pet-friendly, 70% riders-allowed.
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 trucking companies in Milwaukee, Wisconsin
- CDL driver salary in Milwaukee, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
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 July 2026.