Updated May 2026
Best Owner-Operator Companies in Cicero, Illinois (May 2026)
697 owner-operator carriers are hiring in Cicero, Illinois this 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 Cicero, 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 leads the Cicero, Illinois market on combined gross revenue and ranking score this month. YANKEE FREIGHT SYSTEMS LLC's FMCSA score is strongest on hours-of-service compliance — 98th percentile. YANKEE FREIGHT SYSTEMS LLC responds to driver applications more reliably than the Cicero, Illinois median.
#2AD EXPRESS TRUCKING LLC — $2,600/wk
AD EXPRESS TRUCKING LLC tracks as a responsive employer on application-response data. Weekly pay is guaranteed regardless of miles run.
AD EXPRESS TRUCKING LLC stands alone in Cicero, Illinois's top 10 on guaranteed pay — every other ranked carrier here pays per-mile or per-load.
#3WIDER GROUP INC — $6,250/wk
WIDER GROUP INC is active in Cicero, 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.
How drivers spend their time on the road in Cicero, Illinois
Of active CDL postings in Cicero, Illinois this month, 11% are regional and 85% are OTR (long-haul). Local and semi-local routes account for the remaining 4%.
Across Cicero, Illinois CDL postings: 2% with guaranteed pay, 28% dedicated, 92% 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 Cicero, Illinois
- CDL driver salary in Cicero, Illinois
- Best owner-operator companies in Illinois
How we compile these rankings
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 May 2026.