Updated May 2026
Best Owner-Operator Companies in Waukegan, Illinois (May 2026)
Waukegan, Illinois's owner-operator market includes 681 active carriers as of May 2026. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. AD EXPRESS TRUCKING LLC follows at $2,600/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 May 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 YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC is number-one in Waukegan, Illinois this month on the composite ranking. On hours-of-service compliance, the carrier ranks in the 98th percentile per FMCSA SAFER data. Lanefinder's application data flags YANKEE FREIGHT SYSTEMS LLC as a responsive employer.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC responds to driver applications more reliably than the Waukegan, Illinois median. Weekly pay is guaranteed regardless of miles run.
AD EXPRESS TRUCKING LLC is the only Waukegan, Illinois top-10 carrier that guarantees weekly pay regardless of miles run.
#3WIDER GROUP INC — $6,250/wk
WIDER GROUP INC is active in Waukegan, Illinois with a current open requisition.
Also in the top 10: #4 D-LINE TRUCKING INC at $5,750/wk, #5 TAZ TRUCKING INC at $10,999/wk, #6 SWEET EXPRESS LLC at $8,500/wk, #7 INLAND EMPIRE LLC at $7,875/wk, #8 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 TITAN FREIGHT LINES INC at $8,500/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, 28% dedicated, 92% take-truck-home, 73% pet-friendly, 69% riders-allowed.
Where Waukegan, Illinois differs from the Illinois baseline
| Waukegan, Illinois | Illinois top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $5,898 | $5,730 | +3% |
| Pet-friendly fleets | 85% | 80% | +5 pt |
| Riders-allowed policies | 83% | 78% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on pet-friendly fleets: Waukegan, Illinois sits 5 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 May 2026.