Updated September 2026
Best Owner-Operator Companies in Bolingbrook, Illinois (September 2026)
695 carriers are hiring owner-operators in Bolingbrook, Illinois right now, per Lanefinder's September 2026 snapshot. 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 Bolingbrook, 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 Bolingbrook, Illinois ranking with the strongest composite score across pay, safety, benefits, and operational signals. RAY'S TRANSPORT INC's gross weekly revenue ranks in the 95th percentile across Bolingbrook, Illinois. Top FMCSA dimension here is driver fitness, in the 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Bolingbrook, Illinois median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Driver applications get a faster-than-median response in Bolingbrook, Illinois.
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 Bolingbrook, Illinois drivers actually run
The route mix in Bolingbrook, Illinois this month tilts OTR: 11% regional, 86% OTR, 2% local, 1% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Bolingbrook, Illinois postings; dedicated routes at 29%; take-truck-home at 91%. Pet-friendly policies appear at 71% and riders-allowed at 67%.
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 Bolingbrook, Illinois
- CDL driver salary in Bolingbrook, Illinois
- Best owner-operator companies in Illinois
How we compile these rankings
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated September 2026.