Updated November 2026
Best Owner-Operator Companies in Chicago, Illinois (November 2026)
Lanefinder is tracking 689 owner-operator carriers in Chicago, Illinois (November 2026). MONDO MOTION LLC leads with an average gross weekly revenue of $9,250. MAYBACH INTERNATIONAL GROUP INC follows at $3,025/week gross. 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
MONDO MOTION LLC at #1, MAYBACH INTERNATIONAL GROUP INC at #2, and ROLLING ON WHEELS LLC at #3 are new to the top 50 in Chicago, Illinois. RAY'S TRANSPORT INC (was #1), EXPRESS FREIGHT SYSTEMS LLC (was #7), and IGV Express inc (was #10) left the top 50. Average weekly pay moved most at EXPRESS CR INC (up 18.2% from $2,750 to $3,250). Elsewhere in the top 50, 8 carriers joined, 8 left, and 26 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| MONDO MOTION LLC | Not ranked | #1 | New |
| MAYBACH INTERNATIONAL GROUP INC | Not ranked | #2 | New |
| ROLLING ON WHEELS LLC | Not ranked | #3 | New |
| SWEET EXPRESS LLC | #2 | #4 | Down 2 places |
| WINNERS TRANSPORTATION LLC | Not ranked | #5 | New |
| WIDER GROUP INC | #3 | #6 | Down 3 places |
| IKKO LOGISTICS LLC | #8 | #7 | Up 1 place |
| POPE TRANSPORT INC | #4 | #8 | Down 4 places |
| BLUE LIGHTNING LOGISTICS | #5 | #9 | Down 4 places |
| C & G TRANSPORTATION INC | #6 | #10 | Down 4 places |
| M&D TRANSPORT | #9 | #11 | Down 2 places |
| JK MOVING & STORAGE INC | #11 | #12 | Down 1 place |
| TITAN FREIGHT LINES INC | #12 | #13 | Down 1 place |
| HERMES NVC CORP | Not ranked | #14 | New |
| FIVE STAR TRUCKING INC | #13 | #15 | Down 2 places |
| WLC GROUP INC | Not ranked | #16 | New |
| CO Lines Inc | #16 | #17 | Down 1 place |
| SUNGOR TRANSPORTATION INC | #14 | #18 | Down 4 places |
| COMMONWEALTH TRANSPORTATION LLC | #25 | #19 | Up 6 places |
| STEPANOV TRUCKING LLC | Not ranked | #20 | New |
| EXPRESS CR INC | #31 | #23 | Up 8 placesweekly pay up 18.2% ($2,750 → $3,250) |
| ALBA TRANS INC | #27 | #24 | Up 3 places |
| General Transport | #24 | #25 | Down 1 place |
| ICD FREIGHT INC | #29 | #26 | Up 3 places |
| KENNEDY TRANSPORTATION INC | #30 | #27 | Up 3 places |
| AS TRANSPORTATION INC | Not ranked | #28 | New |
| OTRL Recruiting | Not ranked | #29 | New |
| A & H INC | #33 | #30 | Up 3 places |
| D & H CATTLE COMPANY LLC | #32 | #31 | Up 1 place |
| Wynne Transport Service | Not ranked | #32 | New |
| VITAL TRANSPORTATION CORP | #34 | #33 | Up 1 place |
| STAR PARTNERS LLC | Not ranked | #34 | New |
| LANDSHARK LOGISTICS GROUP LLC | #38 | #37 | Up 1 place |
| EOS Trucking Inc. | #37 | #38 | Down 1 place |
| BREEZE TRANSPORTATION INCORPORATED | #40 | #39 | Up 1 place |
| HORIZON TRANSPORTATION | #39 | #40 | Down 1 place |
| TRIPLE G ENTERPRISES INC | #44 | #43 | Up 1 place |
| CYCLE LOGISTICS INC | #43 | #44 | Down 1 place |
| RAY'S TRANSPORT INC | #1 | Not ranked | Dropped out |
| EXPRESS FREIGHT SYSTEMS LLC | #7 | Not ranked | Dropped out |
| IGV Express inc | #10 | Not ranked | Dropped out |
| TNO TRUCKING INC | #15 | Not ranked | Dropped out |
| A&M CARRIERS INC | #17 | Not ranked | Dropped out |
| J & J Oil LLC | #18 | Not ranked | Dropped out |
| KILO METER LOGISTIC INC | #19 | Not ranked | Dropped out |
| BLACK EAGLE EXPRESS LLC | #20 | Not ranked | Dropped out |
| DOGE Trucking LLC | #23 | Not ranked | Dropped out |
| MAX MOVE LLC | #26 | Not ranked | Dropped out |
| WESTERN MOUNTAIN TRANSPORT INC | #28 | Not ranked | Dropped out |
Where owner-operator pay is strongest in Chicago, Illinois this month
The top of the list is MONDO MOTION LLC at $9,250/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1MONDO MOTION LLC — $9,250/wk
MONDO MOTION LLC tops the Chicago, Illinois ranking with the strongest composite score across pay, safety, benefits, and operational signals. MONDO MOTION LLC pays above the 92nd percentile on gross weekly revenue for the Chicago, Illinois market. On hours-of-service compliance, the carrier ranks in the 98th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Chicago, Illinois.
#2MAYBACH INTERNATIONAL GROUP INC — $3,025/wk
MAYBACH INTERNATIONAL GROUP INC is new to the Chicago, Illinois top 50 this month — first appearance in this ranking. MAYBACH INTERNATIONAL GROUP INC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
#3ROLLING ON WHEELS LLC — $6,500/wk
ROLLING ON WHEELS LLC makes its first-time appearance in Chicago, Illinois's ranking this month. ROLLING ON WHEELS LLC pays above the 80th percentile on gross weekly revenue for the Chicago, Illinois market. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 87th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Chicago, Illinois median.
Also in the top 10: #4 SWEET EXPRESS LLC at $8,500/wk, #5 WINNERS TRANSPORTATION LLC at $2,671/wk, #6 WIDER GROUP INC at $6,250/wk, #7 IKKO LOGISTICS LLC at $7,500/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.
How drivers spend their time on the road in Chicago, Illinois
12% of Chicago, Illinois's active CDL postings are regional and 86% are OTR; local plus semi-local accounts for the rest (2%).
Guaranteed pay is on offer at 2% of Chicago, Illinois postings; dedicated routes at 29%; take-truck-home at 91%. Pet-friendly policies appear at 71% and riders-allowed at 67%.
How Chicago, Illinois compares to Illinois
Chicago, Illinois's biggest divergence from Illinois is on average weekly pay, 4% 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 trucking companies in Chicago, Illinois
- CDL driver salary in Chicago, Illinois
- Best owner-operator companies in Illinois
Where this data comes from
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated November 2026.