Updated September 2026
Best Owner-Operator Companies in Chesterfield, Missouri (September 2026)
There are 627 owner-operator carriers currently posting jobs in Chesterfield, Missouri. The ranking below reflects active jobs as of September 2026, not historical pay surveys. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. Missouri freight is shaped by the St. Louis and Kansas City hubs anchoring I-70 / I-44 / I-55 corridors, with the Mississippi and Missouri rivers providing barge access for agricultural and bulk commodity shipments.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
How Chesterfield, Missouri compares to Missouri
Among the figures above, average weekly pay is where Chesterfield, Missouri differs most from Missouri — 17% above statewide.
The owner-operator carriers leading Chesterfield, Missouri this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC is number-one in Chesterfield, Missouri this month on the composite ranking. RAY'S TRANSPORT INC pays above the 90th percentile on gross weekly revenue for the Chesterfield, Missouri market. On driver fitness, the carrier ranks in the 87th percentile per FMCSA SAFER data. Lanefinder's application data flags RAY'S TRANSPORT INC as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. Application-response data flags this carrier as a responsive employer.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. LOAD MONSTER INC tracks as a responsive employer on application-response data.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 WIDER GROUP INC at $6,250/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 C & G TRANSPORTATION INC at $7,500/wk, #8 AIA TRUCKING INC at $3,450/wk, #9 M&D TRANSPORT at $7,000/wk, #10 TITAN FREIGHT LINES INC at $8,500/wk.
What Chesterfield, Missouri drivers actually run
10% of Chesterfield, Missouri's active CDL postings are regional and 90% are OTR; local plus semi-local accounts for the rest (0%).
Across Chesterfield, Missouri CDL postings: 3% with guaranteed pay, 26% dedicated, 93% take-truck-home, 74% pet-friendly, 70% riders-allowed.
Driving CDL in Missouri
Missouri freight is shaped by the St. Louis and Kansas City hubs anchoring the I-70 / I-44 / I-55 corridors. The Mississippi and Missouri rivers provide barge access for agricultural and bulk commodity transfers. St. Louis is one of the older US freight crossroads — the rail-truck interchange there is dense and complicated. Living costs sit comfortably below the national average; Missouri has a low-to-moderate graduated state income tax. Tornado season (March-June) shapes spring dispatch in central and southern MO.
Related guides
- Best trucking companies in Chesterfield, Missouri
- CDL driver salary in Chesterfield, Missouri
- Best owner-operator companies in Missouri
Where this data comes from
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 September 2026.