Updated May 2026
Best Trucking Companies in Chicago, Illinois (May 2026)
Through May 2026, 467 carriers in Chicago, 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. Chicago is the largest US intermodal rail hub, feeding regional truckload across I-80, I-90, and I-55. Local last-mile freight is dense across the western suburbs, with manufacturing and cold-chain loads in the greater metro.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Chicago, 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 is number-one in Chicago, Illinois this month on the composite ranking. KEEP TRUCKING LLC sits in the 95th percentile for weekly pay among Chicago, Illinois carriers. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. Lanefinder's application data flags KEEP TRUCKING LLC as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Chicago, Illinois carriers. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. Driver applications get a faster-than-median response in Chicago, Illinois.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's top FMCSA dimension is hours-of-service compliance, in the 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 CUSTOM COMMODITIES TRANSPORT at $1,750/wk, #10 Badger Express LLC at $1,700/wk.
What Chicago, Illinois drivers actually run
The route mix in Chicago, Illinois this month tilts OTR: 24% regional, 64% OTR, 10% local, 3% semi-local — drawn from active postings, not historical surveys.
Across Chicago, Illinois CDL postings: 2% with guaranteed pay, 26% dedicated, 74% take-truck-home, 60% pet-friendly, 60% riders-allowed.
Chicago, Illinois vs Illinois: the numbers that diverge
Chicago, Illinois's biggest divergence from Illinois is on sign-on bonus availability, 11 points below the state baseline.
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 Chicago, Illinois
- CDL driver salary in Chicago, Illinois
- Best trucking companies in Illinois
The methodology behind the 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.