Updated November 2026
Best Trucking Companies in Chicago, Illinois (November 2026)
Through November 2026, 458 carriers in Chicago, Illinois employ W2 company drivers across the lanes Lanefinder tracks. Herrington Transportation Inc. leads with an average weekly pay of $2,000. McLeod Express LLC follows at $1,520/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 November 2026
SAFE WAY CARRIER LLC at #8 and MNS1 EXPRESS INC at #10 are new to the top 50 in Chicago, Illinois. Biggest climbs: Herrington Transportation Inc. (#39 → #1), FW TRUCKING (#23 → #3), and True Transport Inc. (#18 → #5). Biggest fall: LAWRENCE TRANSPORTATION COMPANY (#1 → #25). Elsewhere in the top 50, 4 carriers joined, 6 left, 37 changed rank, and 1 changed pay or benefits.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #39 | #1 | Up 38 places |
| McLeod Express LLC | #11 | #2 | Up 9 placesweekly pay down 1.9% ($1,550 → $1,520) |
| FW TRUCKING | #23 | #3 | Up 20 places |
| HAZMAT ENVIRONMENTAL GROUP INC | #2 | #4 | Down 2 places |
| True Transport Inc. | #18 | #5 | Up 13 places |
| HandledNow LLC | #3 | #6 | Down 3 places |
| PREMIER TRANSPORTATION | #4 | #7 | Down 3 places |
| SAFE WAY CARRIER LLC | Not ranked | #8 | New |
| JK MOVING & STORAGE INC | #5 | #9 | Down 4 places |
| MNS1 EXPRESS INC | Not ranked | #10 | New |
| Covenant Transport Inc | #6 | #11 | Down 5 places |
| Mountain States L.P. Gas | Not ranked | #12 | New |
| OMAHA TRACK INC | #7 | #13 | Down 6 places |
| DICK LAVY TRUCKING | Not ranked | #14 | New |
| Great Plains Trucking Inc. | #8 | #15 | Down 7 places |
| PRAIRIE FIELD SERVICES LLC | #9 | #16 | Down 7 places |
| Badger Express LLC | #10 | #17 | Down 7 places |
| CUSTOM COMMODITIES TRANSPORT | #13 | #18 | Down 5 places |
| C & G TRANSPORTATION INC | #12 | #19 | Down 7 places |
| Nationwide Rail Services | #17 | #20 | Down 3 places |
| JS HELWIG & SON LLC | #15 | #21 | Down 6 places |
| G & C FOOD DISTRIBUTORS & BROKERS INC | #16 | #22 | Down 6 places |
| G-DIAMOND TRANSPORT INC | #19 | #23 | Down 4 places |
| MC CARRIER LLC | #21 | #24 | Down 3 places |
| LAWRENCE TRANSPORTATION COMPANY | #1 | #25 | Down 24 places |
| ALBA TRANS INC | #20 | #26 | Down 6 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #22 | #27 | Down 5 places |
| HOLLAND ENTERPRISES INC | #27 | #28 | Down 1 place |
| KEN GRAHAM TRUCKING INC | #26 | #30 | Down 4 places |
| CYCLE LOGISTICS INC | #25 | #31 | Down 6 places |
| RIVER CITY TRANSPORT INC | #28 | #32 | Down 4 places |
| A & H INC | #35 | #33 | Up 2 places |
| Wynne Transport Service | Not ranked | #34 | New |
| KAISER TRANSPORT INC | #31 | #35 | Down 4 places |
| AFC Transport, Inc | #34 | #36 | Down 2 places |
| PASCAL CARRIER INC | #33 | #37 | Down 4 places |
| EA EXPRESS LLC | #37 | #38 | Down 1 place |
| BARTELS TRUCK LINE INC | #38 | #39 | Down 1 place |
| LUCKY WORLD INC | Not ranked | #40 | New |
| TRANSPORT HOLDINGS LLC | #46 | #42 | Up 4 places |
| Bertch Cabinet LLC | #40 | #43 | Down 3 places |
| GURTLER INDUSTRIES INC | #42 | #44 | Down 2 places |
| CJC CARRIER LLC | #43 | #45 | Down 2 places |
| TDR TRANSPORT | #44 | #46 | Down 2 places |
| KENNEDY TRANSPORTATION INC | #45 | #47 | Down 2 places |
| SEMO EXPRESS LLC | #47 | #48 | Down 1 place |
| Bakers Express | #48 | #49 | Down 1 place |
| Diaz Stone & Pallet Inc. | #14 | Not ranked | Dropped out |
| H & M TRUCKING INC | #24 | Not ranked | Dropped out |
| WILLIAMS PRESTIGE ENTERPRISE | #30 | Not ranked | Dropped out |
| Alco Transportation Inc | #32 | Not ranked | Dropped out |
| AN ENTERPRISE INC | #36 | Not ranked | Dropped out |
| EAGLE EYE TRUCK LINES LLC | #49 | Not ranked | Dropped out |
Chicago, Illinois's top trucking carriers right now
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. tops the Chicago, Illinois ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 91st percentile for weekly pay in Chicago, Illinois. Application-response data flags this carrier as a responsive employer.
#2McLeod Express LLC — $1,520/wk
McLeod Express LLC is up from #11 last month, one of the largest jumps in the Chicago, Illinois ranking. On unsafe-driving avoidance, the carrier ranks in the 94th percentile per FMCSA SAFER data. Pay is guaranteed on a weekly minimum.
If you want OTR routes without per-mile income variance, McLeod Express LLC is the only Chicago, Illinois top-10 carrier pairing the two.
#3FW TRUCKING — $1,800/wk
FW TRUCKING is up from #23 last month, one of the largest jumps in the Chicago, Illinois ranking. FW TRUCKING's FMCSA score is strongest on unsafe-driving avoidance — 90th percentile.
Also in the top 10: #4 HAZMAT ENVIRONMENTAL GROUP INC at $2,100/wk, #5 True Transport Inc. at $2,250/wk, #6 HandledNow LLC at $1,550/wk, #7 PREMIER TRANSPORTATION at $1,950/wk, #8 SAFE WAY CARRIER LLC at $2,100/wk, #9 JK MOVING & STORAGE INC at $2,200/wk, #10 MNS1 EXPRESS INC at $2,050/wk.
What Chicago, Illinois drivers actually run
The route mix in Chicago, Illinois this month tilts OTR: 24% regional, 62% OTR, 10% local, 3% semi-local — drawn from active postings, not historical surveys.
Across Chicago, Illinois CDL postings: 4% with guaranteed pay, 28% dedicated, 73% take-truck-home, 59% pet-friendly, 60% riders-allowed.
Chicago, Illinois vs Illinois: the numbers that diverge
| Chicago, Illinois | Illinois top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 33% | 41% | -8 pt |
| Dedicated routes | 33% | 41% | -8 pt |
Source: Lanefinder index, November 2026
Chicago, Illinois's biggest divergence from Illinois is on sign-on bonus availability, 8 points below the state baseline.
Driving CDL in Chicago
Chicago is the largest US intermodal rail hub — a huge percentage of national freight passes through. Metro lanes pay well but congestion on I-80, I-90, I-294 is consistent enough to be a real income variable. Winter is severe (lake-effect snow, salt corrosion). Cost of living is moderate. Tollway transponder is essentially required.
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 November 2026.