Updated September 2026
Best Owner-Operator Companies in Des Plaines, Illinois (September 2026)
694 owner-operator carriers are currently posting jobs in Des Plaines, Illinois 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.
Des Plaines, Illinois's top owner-operator carriers right now
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 Des Plaines, Illinois this month on the composite ranking. RAY'S TRANSPORT INC sits in the 96th percentile for gross weekly revenue among Des Plaines, Illinois carriers. RAY'S TRANSPORT INC's top FMCSA dimension is driver fitness, in the 87th percentile. Driver applications get a faster-than-median response in Des Plaines, Illinois.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#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.
What Des Plaines, Illinois drivers actually run
Of active CDL postings in Des Plaines, Illinois this month, 12% are regional and 85% are OTR (long-haul). Local and semi-local routes account for the remaining 3%.
Across Des Plaines, Illinois CDL postings: 2% with guaranteed pay, 29% dedicated, 91% take-truck-home, 71% pet-friendly, 67% 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 Des Plaines, Illinois
- CDL driver salary in Des Plaines, Illinois
- Best owner-operator companies in Illinois
The methodology behind the rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated September 2026.