Updated May 2026
Best Trucking Companies in Oak Park, Illinois (May 2026)
Through May 2026, 468 carriers in Oak Park, Illinois employ W2 company drivers across the lanes Lanefinder tracks. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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.
Oak Park, Illinois's top trucking carriers right now
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC leads the Oak Park, Illinois market on combined pay and ranking score this month. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Oak Park, Illinois market. KEEP TRUCKING LLC's FMCSA score is strongest on controlled-substances compliance — 88th percentile. Driver applications get a faster-than-median response in Oak Park, Illinois.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 92nd percentile on weekly pay for the Oak Park, Illinois market. On unsafe-driving avoidance, the carrier ranks in the 99th percentile per FMCSA SAFER data. Lanefinder's application data flags True Transport Inc. as a responsive employer.
True Transport Inc. actually pays more weekly than the top-ranked carrier — $2,250/week.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's FMCSA score is strongest on hours-of-service compliance — 94th percentile.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 OMAHA TRACK INC at $2,000/wk, #6 Great Plains Trucking Inc. at $1,750/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 PREMIER TRANSPORTATION at $1,700/wk, #9 Badger Express LLC at $1,700/wk, #10 CUSTOM COMMODITIES TRANSPORT at $1,750/wk.
What Oak Park, Illinois drivers actually run
The route mix in Oak Park, Illinois this month tilts OTR: 23% regional, 63% OTR, 10% local, 3% semi-local — drawn from active postings, not historical surveys.
Across Oak Park, Illinois CDL postings: 2% with guaranteed pay, 26% dedicated, 73% take-truck-home, 59% pet-friendly, 59% riders-allowed.
Oak Park, Illinois vs Illinois: the numbers that diverge
| Oak Park, Illinois | Illinois top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 35% | 44% | -9 pt |
| Take-truck-home | 90% | 85% | +5 pt |
Source: Lanefinder index, May 2026
Among the figures above, sign-on bonus availability is where Oak Park, Illinois differs most from Illinois — 9 points below 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 owner-operator companies in Oak Park, Illinois
- CDL driver salary in Oak Park, Illinois
- Best trucking companies in Illinois
How we compile these rankings
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated May 2026.