Updated May 2026
Best Owner-Operator Companies in Oshkosh, Wisconsin (May 2026)
587 owner-operator carriers are hiring in Oshkosh, Wisconsin this May 2026. 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. Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison, with dairy and food processing as the dominant outbound commodity and paper and packaging manufacturing in the Fox River Valley generating consistent industrial loads.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
How Oshkosh, Wisconsin compares to Wisconsin
| Oshkosh, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $7,245 | $5,399 | +34% |
| Riders-allowed policies | 90% | 79% | +11 pt |
Source: Lanefinder index, May 2026
Among the figures above, average weekly pay is where Oshkosh, Wisconsin differs most from Wisconsin — 34% above statewide.
Oshkosh, 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 tops the Oshkosh, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Top FMCSA dimension here is hours-of-service compliance, in the 98th percentile. Application-response data flags this carrier as a responsive employer.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC responds to driver applications more reliably than the Oshkosh, Wisconsin median. AD EXPRESS TRUCKING LLC offers a guaranteed weekly minimum.
For guaranteed weekly pay, AD EXPRESS TRUCKING LLC is the only top-10 Oshkosh, Wisconsin carrier offering it.
#3Zmile Inc — $2,925/wk
Zmile Inc's top FMCSA dimension is hours-of-service compliance, in the 98th percentile. Driver applications get a faster-than-median response in Oshkosh, Wisconsin.
Also in the top 10: #4 D-LINE TRUCKING INC at $5,750/wk, #5 WIDER GROUP INC at $6,250/wk, #6 TAZ TRUCKING INC at $10,999/wk, #7 SWEET EXPRESS LLC at $8,500/wk, #8 INLAND EMPIRE LLC at $7,875/wk, #9 Ali Star Inc at $10,000/wk, #10 BLUE LIGHTNING LOGISTICS at $7,000/wk.
What Oshkosh, Wisconsin drivers actually run
Of active CDL postings in Oshkosh, Wisconsin this month, 7% are regional and 92% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 1% of Oshkosh, 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 Oshkosh, Wisconsin
- CDL driver salary in Oshkosh, Wisconsin
- Best owner-operator companies in Wisconsin
The methodology behind the rankings
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated May 2026.