Updated September 2026
Best Owner-Operator Companies in Waukegan, Illinois (September 2026)
Waukegan, Illinois's owner-operator market includes 682 active carriers as of 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. 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 Waukegan, 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 is number-one in Waukegan, Illinois this month on the composite ranking. Pay sits above the 91st percentile in the Waukegan, Illinois market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. Lanefinder's application data flags RAY'S TRANSPORT INC as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. Application-response data flags this carrier as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. LOAD MONSTER INC tracks as a responsive employer on application-response data.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 WIDER GROUP INC at $6,250/wk, #7 POPE TRANSPORT INC at $7,000/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 AIA TRUCKING INC at $3,450/wk.
Lane mix and benefits across Waukegan, Illinois
11% of Waukegan, Illinois's active CDL postings are regional and 86% are OTR; local plus semi-local accounts for the rest (3%).
Across Waukegan, Illinois CDL postings: 2% with guaranteed pay, 29% dedicated, 91% take-truck-home, 72% pet-friendly, 68% 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 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 September 2026.