Updated July 2026
Best Owner-Operator Companies in Illinois (July 2026)
797 carriers in Illinois are actively recruiting owner-operators as of July 2026. Each is scored on a composite of compensation, FMCSA safety, benefits, and operational performance. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. WINNERS TRANSPORTATION LLC follows at $2,437/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 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 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 Illinois market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
#3Performance Trucking Inc — $8,000/wk
Performance Trucking Inc sits in the 94th percentile for gross weekly revenue among Illinois carriers.
Also in the top 10: #4 OVERLOG INC at $3,145/wk, #5 Tradewinds Logistics at $5,500/wk, #6 SWEET EXPRESS LLC at $8,500/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 JK MOVING & STORAGE INC at $4,975/wk, #10 TP TRUCKING at $8,500/wk.
Lane mix and benefits across Illinois
14% of Illinois's active CDL postings are regional and 82% are OTR; local plus semi-local accounts for the rest (4%).
Across Illinois CDL postings: 2% with guaranteed pay, 29% dedicated, 90% take-truck-home, 70% pet-friendly, 66% 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 Illinois
- CDL driver salary in Illinois
- Best owner-operator companies in the United States
How we compile these rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated July 2026.