Updated November 2026
Best Owner-Operator Companies in Milwaukee, Wisconsin (November 2026)
There are 615 owner-operator carriers currently posting jobs in Milwaukee, Wisconsin. The ranking below reflects active jobs as of November 2026, not historical pay surveys. MONDO MOTION LLC leads with an average gross weekly revenue of $9,250. MAYBACH INTERNATIONAL GROUP INC follows at $3,025/week gross. Milwaukee anchors I-94 on Lake Michigan with a port handling dry bulk and breakbulk cargo, with a dense manufacturing base in industrial goods and packaging, and Midwest distribution via I-94 and I-43.
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 Milwaukee, Wisconsin. RAY'S TRANSPORT INC (was #1) and EXPRESS FREIGHT SYSTEMS LLC (was #2) 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, 7 carriers joined, 8 left, and 31 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 | #3 | #4 | Down 1 place |
| WINNERS TRANSPORTATION LLC | Not ranked | #5 | New |
| WIDER GROUP INC | #4 | #6 | Down 2 places |
| IKKO LOGISTICS LLC | #8 | #7 | Up 1 place |
| POPE TRANSPORT INC | #5 | #8 | Down 3 places |
| BLUE LIGHTNING LOGISTICS | #6 | #9 | Down 3 places |
| C & G TRANSPORTATION INC | #7 | #10 | Down 3 places |
| JK MOVING & STORAGE INC | #10 | #11 | Down 1 place |
| M&D TRANSPORT | #9 | #12 | Down 3 places |
| MCDERMID TRANSPORTATION INC | #14 | #13 | Up 1 place |
| TITAN FREIGHT LINES INC | #11 | #14 | Down 3 places |
| Goldway Trans LLC | #13 | #15 | Down 2 places |
| ITF Group | #15 | #16 | Down 1 place |
| HERMES NVC CORP | Not ranked | #17 | New |
| FIVE STAR TRUCKING INC | #16 | #18 | Down 2 places |
| LUXOR DRIVE INC | Not ranked | #19 | New |
| Brenny Specialized Inc | #19 | #20 | Down 1 place |
| Blue Diamond Transportation LLC | #17 | #21 | Down 4 places |
| WLC GROUP INC | Not ranked | #22 | New |
| CO Lines Inc | #21 | #23 | Down 2 places |
| SUNGOR TRANSPORTATION INC | #18 | #24 | Down 6 places |
| SUPERTRANSPORT LLC | #26 | #25 | Up 1 place |
| BIG JOHN EXPEDITED INC | #22 | #26 | Down 4 places |
| LEGACY CARGO LLC | #25 | #27 | Down 2 places |
| Lois Yoder Trucking | #29 | #28 | Up 1 place |
| J & J Oil LLC | #24 | #29 | Down 5 places |
| EXPRESS CR INC | #34 | #30 | Up 4 placesweekly pay up 18.2% ($2,750 → $3,250) |
| ALBA TRANS INC | #33 | #31 | Up 2 places |
| COMMONWEALTH TRANSPORTATION LLC | #36 | #32 | Up 4 places |
| AS TRANSPORTATION INC | Not ranked | #33 | New |
| A & H INC | #38 | #34 | Up 4 places |
| OTRL Recruiting | Not ranked | #35 | New |
| D & H CATTLE COMPANY LLC | #37 | #36 | Up 1 place |
| VITAL TRANSPORTATION CORP | #39 | #37 | Up 2 places |
| LINESTAR EXPRESS LLC | #35 | #38 | Down 3 places |
| STAR PARTNERS LLC | Not ranked | #39 | New |
| LANDSHARK LOGISTICS GROUP LLC | #43 | #40 | Up 3 places |
| AN ENTERPRISE INC | #40 | #42 | Down 2 places |
| EOS Trucking Inc. | #42 | #43 | Down 1 place |
| RAY'S TRANSPORT INC | #1 | Not ranked | Dropped out |
| EXPRESS FREIGHT SYSTEMS LLC | #2 | Not ranked | Dropped out |
| IGV Express inc | #12 | Not ranked | Dropped out |
| TNO TRUCKING INC | #20 | Not ranked | Dropped out |
| A&M CARRIERS INC | #23 | Not ranked | Dropped out |
| KILO METER LOGISTIC INC | #27 | Not ranked | Dropped out |
| BLACK EAGLE EXPRESS LLC | #28 | Not ranked | Dropped out |
| DOGE Trucking LLC | #30 | Not ranked | Dropped out |
| MAX MOVE LLC | #31 | Not ranked | Dropped out |
| WESTERN MOUNTAIN TRANSPORT INC | #32 | Not ranked | Dropped out |
Where owner-operator pay is strongest in Milwaukee, Wisconsin 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 Milwaukee, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Gross weekly revenue here lands in the 96th percentile across Milwaukee, Wisconsin. MONDO MOTION LLC ranks in the 98th percentile for hours-of-service compliance on FMCSA SAFER data. MONDO MOTION LLC tracks as a responsive employer on application-response data.
#2MAYBACH INTERNATIONAL GROUP INC — $3,025/wk
MAYBACH INTERNATIONAL GROUP INC is new to the Milwaukee, Wisconsin top 50 this month — first appearance in this ranking. On driver fitness, the carrier ranks in the 96th percentile per FMCSA SAFER data. MAYBACH INTERNATIONAL GROUP INC responds to driver applications more reliably than the Milwaukee, Wisconsin median.
#3ROLLING ON WHEELS LLC — $6,500/wk
ROLLING ON WHEELS LLC is new to the Milwaukee, Wisconsin top 50 this month — first appearance in this ranking. ROLLING ON WHEELS LLC ranks in the 87th percentile for driver fitness on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
Also in the top 10: #4 SWEET EXPRESS LLC at $8,500/wk, #5 WINNERS TRANSPORTATION LLC at $2,657/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.
What Milwaukee, Wisconsin drivers actually run
The route mix in Milwaukee, Wisconsin this month tilts OTR: 9% regional, 90% OTR, 1% local, 0% semi-local — drawn from active postings, not historical surveys.
Across Milwaukee, Wisconsin CDL postings: 2% with guaranteed pay, 28% dedicated, 92% take-truck-home, 73% pet-friendly, 69% riders-allowed.
How Milwaukee, Wisconsin compares to Wisconsin
| Milwaukee, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,360 | $5,222 | +22% |
| Riders-allowed policies | 86% | 76% | +10 pt |
Source: Lanefinder index, November 2026
The largest gap is on average weekly pay: Milwaukee, Wisconsin sits 22% above the Wisconsin baseline.
Driving CDL in Milwaukee
Milwaukee anchors southeastern Wisconsin on I-94 / I-43 / I-794. Manufacturing (Harley-Davidson HQ, GE HealthCare's largest US manufacturing and engineering footprint (consolidating into the Waukesha campus; corporate HQ now in Chicago)), Northwestern Mutual HQ, and distribution serving the Lake Michigan corridor drive freight. Cost of living is moderate. Lake-effect snow off Lake Michigan affects the city in winter; salt corrosion is real.
Driving CDL in Wisconsin
Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison. Dairy and food processing are dominant outbound commodities — Wisconsin's reefer freight is a national-scale segment. Paper and packaging manufacturing in the Fox River Valley generates consistent industrial loads. Great Lakes ports at Green Bay and Superior handle bulk cargo. Cost of living is moderate. Wisconsin has a high graduated state income tax. Winter is severe — lake-effect snow off Lake Michigan affects the eastern third of the state; ice and salt corrosion eat equipment faster than southern states.
Related guides
- Best trucking companies in Milwaukee, Wisconsin
- CDL driver salary in Milwaukee, Wisconsin
- Best owner-operator companies in Wisconsin
How we compile these rankings
The score is built from four buckets. Thirty percent compensation, drawn from real active job postings and modified by bonus and settlement structure. Twenty-five percent safety, from FMCSA SAFER. Twenty-five percent benefits, scored hiring-type-aware. Twenty percent operational performance, drawn from how carriers actually behave toward applicants. Updated November 2026.