Updated July 2026
Best Owner-Operator Companies in Waukegan, Illinois (July 2026)
Waukegan, Illinois's owner-operator market includes 674 active carriers as of July 2026. 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 Waukegan, 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 is number-one in Waukegan, Illinois this month on the composite ranking. ROLLING ON WHEELS LLC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#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.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 86th percentile on gross weekly revenue for the Waukegan, Illinois market.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 WIDER GROUP INC at $6,250/wk, #7 OVERLOG INC at $3,145/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 POPE TRANSPORT INC at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
Lane mix and benefits across Waukegan, Illinois
11% of Waukegan, Illinois's active CDL postings are regional and 87% are OTR; local plus semi-local accounts for the rest (2%).
Across Waukegan, Illinois CDL postings: 2% with guaranteed pay, 28% dedicated, 91% take-truck-home, 73% pet-friendly, 69% riders-allowed.
Where Waukegan, Illinois differs from the Illinois baseline
The largest gap is on riders-allowed policies: Waukegan, Illinois sits 6 points above the Illinois 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 Waukegan, Illinois
- CDL driver salary in Waukegan, Illinois
- Best owner-operator companies in Illinois
How we compile these rankings
The composite score is 30% compensation, 25% FMCSA safety, 25% benefits, and 20% operational performance. Pay percentiles are computed against carriers currently hiring in each market; FMCSA percentiles come from SAFER and weight unsafe-driving and hours-of-service violations 2× heavier than the other three dimensions. Updated July 2026.