Regional CDL Driver Jobs in Wisconsin July 2026

CDL DNA

Team Dry Van - Contracted freight - 7,000+ miles

Hiring in Wisconsin and 46 other locations
Dedicated, OTR, Regional
3 weeks out
$0.76 Per mile

You can expect earning $5,320 - $5,475 per week consistently.
We promise 7,000+ miles per week and consistent work
Company will pay for your drug test, flight and accommodations to help you join our team effortlessly.

Drivers Top Choice

Consistent Contracted Freight

300+ Trucks Fleet

Eos Inc.

CDL-A Lease Purchase | $0 Down, No Credit Check

Hiring in Wisconsin and 46 other locations
OTR, Regional
2 weeks out
$2,200 - 2,500 Per week

Gross pay: $6,000-$8,000 weekly. Earn approx. $2,200-$2,500 weekly (after all lease cost). Lease Purchase Pay: 73% of revenue. Paid 2-day Orientation
$0 Down, No Credit Check. Home every 2 weeks.Truck Payments: typically range from $650-$1,040/week. Inspection and referral bonuses.
Lease Op Charges fixed cost: $475/week total. Pet & Rider policies. Medical, Dental, Vision, and 401K offered through 3rd parties.

Ashley Distribution Services LTD

Regional OTR CDL-A Truck Driver | $81,000/year

Hiring in Wisconsin and 46 other locations
OTR, Regional
Weekly
$81,000 Per year

Top 25% of drivers earn $81,000 annually. Regional routes. Regular 34-hour resets at home. No-touch freight.
Mix of live load/unload and drop and hook accounts. Consistent, high weekly miles. Excellent, premium equipment.
Generous benefits package: Can add up to an additional 27% on top of your base salary! Job stability.

AAA Transit Group LLC

CDL A Owner Operator St Louis and Midwest region

Hiring in Wisconsin and 11 other locations
Local, OTR, Regional
Flexible
80% Of gross

We are an established trucking company, with a solid reputation in the industry
Additionally, we have our own brokerage, which gives us access to high paying loads
We have several contracts that we are looking to fulfill and grow, while we expand throughout the midwest.

Jeep Transport LLC

CDL A Company Driver | OTR, Regional, Dedicated

Hiring in Wisconsin and 46 other locations
OTR, Regional
2 weeks out, 3 weeks out
$0.60 Per mile

Equipment: 2020-2024 automatic Freightliner Cascadia
Additional Pay: Extra Stops, Layover, and Detention
Pets Friendly. APU, Fridge, Power Inverter in trucks

Dedicated Local and Regional Runs

Blackwell's Trucking Inc.

Regional Dry Van CDL A Drivers

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,300 - 1,575 Per week

Mostly Drop & Hook
Steady customer interaction on daily bases
Driver will make deliveries to dedicated vendors and warehouses

Central States Mfg.

Regional Flatbed CDL A - Claysburg

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$80,000 Per year

Average driver earns $82,000 in total compensation per year
Annual 5% Profit-Sharing Bonus
Home EVERY weekend & paid holidays

KLM Trucking

Regional | CDL-A Truck Driver | Dedicated Lanes

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,445 - 1,540 Per week

Mix of flatbed and van trailers. HazMat and TWIC required
Solo dedicated account. Regional operating area
Paid orientation and job specific training

JK Rose Logistics

Regional | CDL-A Truck Driver | Dedicated Lanes

Hiring in Wisconsin and 47 other locations
Regional
Flexible
$1,435 - 1,540 Per week

Load securement is required .Operate within a regional area
Assigned automatic sleeper cab trucks
Flatbed trailers. Limited number of spots available

Odysseia

CDL C Sprinter Van / Cargo VanOwner Operator

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,000 Per week

No authority; NO MC. Be ready to make long-distance/other loads; local - rarely and occasionally.
Clean and tidy vans are preferred - no debris, spots, dents, etc.
Weekly payment, no hidden fees - you get paid your rate fully.

KLM Trucking

Semi-Local | Flatbed | CDL-A Truck Driver

Hiring in Wisconsin and 47 other locations
Local, Regional
Weekly
$1,655 Per week

Solo dedicated account. Regional operating area. Home most days
Drivers will strap all loads. Home most days.
Automatic sleeper cab tractors. Flatbed trailers

Pelts Xpress

CDL A Owner Operator | Regional Runs

Hiring in Wisconsin and 46 other locations
OTR, Regional
Flexible
88% Of gross

Consistent direct customer freight, both Regional and OTR!
88% of gross revenue. Up to $0.40 fuel discount (100% to the owner)
Assistance with Plates & Registration. Warm and welcoming team

FREE 30 Days Trailer Rent

Up to $0.40 fuel discount (100% to the owner)

Plates & Registration Program

Best Way Transportation LLC

Owner Operator/Fleet Owners -Flatbed

Hiring in Wisconsin and 47 other locations
OTR, Regional
Flexible
$3,000 Per week

MUST OWN YOUR OWN TRUCK W/TRAILER also POWER ONLY
We are skilled with years of experience in driving and dispatching so we understand how important compliance, auditing, and recordkeeping
ACCEPTING Owner Operators NATIONWIDE. MUST HAVE YOUR OWN AUTHORITY!

Ferrous Metal Transfer Co.

OTR FLATBED TRUCK DRIVER

Hiring in Wisconsin and 47 other locations
OTR, Regional
Weekly
27% Of gross

Exceptional Bonus plan! Comprehensive Benefits Package
Freight Type : Flatbed freight; steel coils, steel sheets, steel bars, etc.
Bonuses available: Attendance ($185/quarterly), Safety($100/quarterly), Yearly Retention($1000/year)

Andrus Transportation Services

CDL-A Flatbed Driver - Western Fleet

Hiring in Wisconsin and 47 other locations
OTR, Regional
Flexible
$74,100 - 84,500 Per year
/
$1,625 Per week

Talk to your recruiter about lanes throughout the following states: WA, OR, ID, NV, CA, UT, CO, WY, AZ, NM
Immediate Openings - Flatbed Drivers in the Western States
Fully Loaded - with premium interiors, ELSs, Prepass, Qualcomm, and Transflow

Regional CDL driver jobs in Wisconsin