Updated September 2026
Best Owner-Operator Companies in Oak Lawn, Illinois (September 2026)
697 carriers in Oak Lawn, Illinois are actively recruiting owner-operators as of September 2026. Each is scored on a composite of compensation, FMCSA safety, benefits, and operational performance. 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 Oak Lawn, 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 Oak Lawn, Illinois market on combined gross revenue and ranking score this month. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 95th percentile across Oak Lawn, Illinois. Top FMCSA dimension here is driver fitness, in the 87th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Oak Lawn, Illinois median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Lanefinder's application data flags LOAD MONSTER INC 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 Oak Lawn, Illinois
Of active CDL postings in Oak Lawn, Illinois this month, 11% are regional and 86% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Guaranteed pay is on offer at 2% of Oak Lawn, Illinois postings; dedicated routes at 29%; take-truck-home at 91%. Pet-friendly policies appear at 71% and riders-allowed at 67%.
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 Oak Lawn, Illinois
- CDL driver salary in Oak Lawn, Illinois
- Best owner-operator companies in Illinois
How we compile these rankings
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 September 2026.