Updated September 2026
Best Owner-Operator Companies in Wheeling, Illinois (September 2026)
690 owner-operator carriers are hiring in Wheeling, Illinois this September 2026. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. Illinois anchors the US rail and truck network through Chicago, the largest intermodal hub in North America, with I-80 / I-90 / I-55 feeding a dense concentration of manufacturing, warehousing, and cold-chain freight.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where owner-operator pay is strongest in Wheeling, Illinois this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC leads the Wheeling, Illinois market on combined gross revenue and ranking score this month. Pay sits above the 91st percentile in the Wheeling, Illinois market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Wheeling, Illinois median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 SWEET EXPRESS LLC at $8,500/wk, #7 WIDER GROUP INC at $6,250/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
How drivers spend their time on the road in Wheeling, Illinois
12% of Wheeling, Illinois's active CDL postings are regional and 85% are OTR; local plus semi-local accounts for the rest (3%).
Across Wheeling, Illinois CDL postings: 2% with guaranteed pay, 29% dedicated, 91% take-truck-home, 71% pet-friendly, 67% riders-allowed.
Driving CDL in Illinois
Illinois is one of the most strategically located CDL states — Chicago is the largest US intermodal rail hub, so a huge percentage of national freight passes through. The metro lanes pay well but congestion on I-80, I-90, and I-294 is consistent enough to be a real income variable. Outside the Chicago metro, downstate Illinois looks much more like Iowa or Indiana — agricultural freight, less density, easier driving. State income tax is moderate. The winter operational profile is severe: lake-effect snow, road salt, and the freezing-thawing cycle eat equipment faster than most southern states.
Related guides
- Best trucking companies in Wheeling, Illinois
- CDL driver salary in Wheeling, Illinois
- Best owner-operator companies in Illinois
Where this data comes from
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated September 2026.