Updated September 2026
Best Owner-Operator Companies in DeKalb, Illinois (September 2026)
Through September 2026, 680 carriers in DeKalb, Illinois contract owner-operators across the lanes Lanefinder tracks. 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 DeKalb, 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 tops the DeKalb, Illinois ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 90th percentile in the DeKalb, Illinois market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. Driver applications get a faster-than-median response in DeKalb, Illinois.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/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 POPE TRANSPORT INC at $7,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
How drivers spend their time on the road in DeKalb, Illinois
The route mix in DeKalb, Illinois this month tilts OTR: 10% regional, 87% OTR, 2% local, 0% semi-local — drawn from active postings, not historical surveys.
Across DeKalb, Illinois CDL postings: 2% with guaranteed pay, 28% dedicated, 91% take-truck-home, 72% pet-friendly, 68% riders-allowed.
Where DeKalb, Illinois differs from the Illinois baseline
| DeKalb, Illinois | Illinois top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $5,515 | $5,355 | +3% |
| Pet-friendly fleets | 86% | 78% | +8 pt |
| Riders-allowed policies | 88% | 80% | +8 pt |
Source: Lanefinder index, September 2026
Among the figures above, pet-friendly fleets is where DeKalb, Illinois differs most from Illinois — 8 points above statewide.
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 DeKalb, Illinois
- CDL driver salary in DeKalb, Illinois
- Best owner-operator companies in Illinois
Where this data comes from
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated September 2026.