Updated May 2026
Best Trucking Companies in Naperville, Illinois (May 2026)
As of May 2026, 475 carriers in Naperville, Illinois are posting active jobs for W2 company drivers. 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.
The trucking companies leading Naperville, Illinois this month
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 Naperville, Illinois market on combined pay and ranking score this month. Pay sits above the 90th percentile in the Naperville, Illinois market. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. KEEP TRUCKING LLC responds to driver applications more reliably than the Naperville, Illinois median.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Naperville, Illinois carriers. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 99th percentile. True Transport Inc. responds to driver applications more reliably than the Naperville, Illinois median.
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 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 CUSTOM COMMODITIES TRANSPORT at $1,750/wk, #10 Badger Express LLC at $1,700/wk.
How drivers spend their time on the road in Naperville, Illinois
24% of Naperville, Illinois's active CDL postings are regional and 63% are OTR; local plus semi-local accounts for the rest (13%).
Across Naperville, Illinois CDL postings: 2% with guaranteed pay, 27% dedicated, 74% take-truck-home, 59% pet-friendly, 60% riders-allowed.
How Naperville, Illinois compares to Illinois
Among the figures above, sign-on bonus availability is where Naperville, 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 Naperville, Illinois
- CDL driver salary in Naperville, Illinois
- Best trucking 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 May 2026.