Updated May 2026
Best Owner-Operator Companies in Madison, Wisconsin (May 2026)
As of May 2026, 610 carriers in Madison, Wisconsin are posting active jobs for owner-operators. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. AD EXPRESS TRUCKING LLC follows at $2,600/week gross. Madison sits at the I-90 / I-94 junction in south-central Wisconsin, with large-scale dairy and food processing, university institutional procurement, and manufacturing distribution for the Wisconsin River Valley corridor.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Madison, Wisconsin vs Wisconsin: the numbers that diverge
| Madison, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $7,000 | $5,399 | +30% |
| Riders-allowed policies | 88% | 79% | +9 pt |
Source: Lanefinder index, May 2026
Among the figures above, average weekly pay is where Madison, Wisconsin differs most from Wisconsin — 30% above statewide.
Madison, Wisconsin's top owner-operator carriers right now
The top of the list is YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC leads the Madison, Wisconsin market on combined gross revenue and ranking score this month. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC tracks as a responsive employer on application-response data. AD EXPRESS TRUCKING LLC offers a guaranteed weekly minimum.
For guaranteed weekly pay, AD EXPRESS TRUCKING LLC is the only top-10 Madison, Wisconsin carrier offering it.
#3D-LINE TRUCKING INC — $5,750/wk
D-LINE TRUCKING INC tracks as a responsive employer on application-response data.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 TAZ TRUCKING INC at $10,999/wk, #6 Zmile Inc at $2,175/wk, #7 INLAND EMPIRE LLC at $7,875/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 Ali Star Inc at $10,000/wk, #10 BLUE LIGHTNING LOGISTICS at $7,000/wk.
How drivers spend their time on the road in Madison, Wisconsin
7% of Madison, Wisconsin's active CDL postings are regional and 91% are OTR; local plus semi-local accounts for the rest (2%).
Guaranteed pay is on offer at 2% of Madison, Wisconsin postings; dedicated routes at 26%; take-truck-home at 94%. Pet-friendly policies appear at 75% and riders-allowed at 71%.
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 Madison, Wisconsin
- CDL driver salary in Madison, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated May 2026.