Updated September 2026
Best Owner-Operator Companies in Chicago, Illinois (September 2026)
Lanefinder is tracking 693 owner-operator carriers in Chicago, Illinois (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. Chicago is the largest US intermodal rail hub, feeding regional truckload across I-80, I-90, and I-55. Local last-mile freight is dense across the western suburbs, with manufacturing and cold-chain loads in the greater metro.
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 Chicago, 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 Chicago, Illinois market on combined gross revenue and ranking score this month. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 96th percentile across Chicago, Illinois. Top FMCSA dimension here is driver fitness, in the 87th percentile. RAY'S TRANSPORT INC tracks as a responsive employer on application-response data.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. LOAD MONSTER INC responds to driver applications more reliably than the Chicago, Illinois median.
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 Chicago, Illinois
12% of Chicago, Illinois's active CDL postings are regional and 86% are OTR; local plus semi-local accounts for the rest (2%).
Guaranteed pay is on offer at 2% of Chicago, 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 Chicago, Illinois
- CDL driver salary in Chicago, Illinois
- Best owner-operator companies in Illinois
Where this data comes from
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 September 2026.