Updated July 2026
Best Owner-Operator Companies in Chicago, Illinois (July 2026)
Lanefinder is tracking 680 owner-operator carriers in Chicago, Illinois (July 2026). ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. Performance Trucking Inc follows at $8,000/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 July 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 ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC leads the Chicago, Illinois market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Chicago, Illinois median.
#2Performance Trucking Inc — $8,000/wk
Performance Trucking Inc pays above the 88th percentile on gross weekly revenue for the Chicago, Illinois market.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 86th percentile on gross weekly revenue for the Chicago, Illinois market.
Also in the top 10: #4 WINNERS TRANSPORTATION LLC at $2,437/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 OVERLOG INC at $3,145/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 POPE TRANSPORT INC at $7,000/wk.
How drivers spend their time on the road in Chicago, Illinois
11% of Chicago, Illinois's active CDL postings are regional and 86% are OTR; local plus semi-local accounts for the rest (3%).
Guaranteed pay is on offer at 2% of Chicago, Illinois postings; dedicated routes at 28%; take-truck-home at 91%. Pet-friendly policies appear at 72% and riders-allowed at 68%.
How Chicago, Illinois compares to Illinois
Chicago, Illinois's biggest divergence from Illinois is on riders-allowed policies, 6 points above the state baseline.
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 July 2026.