Regional CDL Driver Jobs in Wisconsin June 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

Most of the contracted loads is mail, mixed with costco, walmart and amazon.
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

Ruan Transportation Management Systems

Regional CDL-A Truck Driver | Dry Van | 57 CPM

Hiring in Wisconsin and 2 other locations
Regional
Weekly
$0.57 Per mile

Get paid weekly with activity-based pay of $0.57 per mile, $21 per stop, $42 total for pick and delivery, and $25 per diem!
Drivers will average $1,600 gross income per week or $85,000 per year. No-touch freight.
Enjoy a Monday through Friday schedule with weekends off! Operate a 2024 Penske Sleeper and 53ft dry van.

Just Trucking Services

CDL A - Lease to purchase with $0 Down

Hiring in Wisconsin and 45 other locations
OTR, Regional
Flexible
$90,000 - 120,000 Per year

OTR drivers wanted willing to start their own business.
Low weekly payments. Weekly gross 6k-8k. No hidden fees
Start and grow your trucking business with us!

No Credit Check

Get One or Multiple Trucks

$0 Down for Truck and Trailer

Hittman Transport Services, Inc.

Owner Operators CDL A Team Truck Drivers

Hiring in Wisconsin and 46 other locations
Regional
Daily, Flexible
$10,000 Per week

Hittman Transport Services, Inc. is contracting owner operators.
Teams make up to $10,000 weekly. Quarterly Fuel Discount, plus Discounts at the pump.
Hittman Transport pays for the yearly expenses: tolls, fuel tax, tractor washes...

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
Flexible Home Time. No Force Dispatch. No Hazmat Loads
Pets Friendly. APU, Fridge, Power Inverter in trucks

Dedicated Local and Regional Runs

Just Trucking Services

CDL A Owner Operators For Dedicated Midwest Lanes

Hiring in Wisconsin and 3 other locations
Regional
Flexible
$7,000 - 9,000 Per week

Consistent year-around freight. Spots are very limited
Looking for Owner Operators with or without trailer
For specific lanes information, please press "Apply now" to leave your contact information.

Year Around Contract

High Paying Dedicated Lanes

Only For Owner Operators

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
401(k) plan w/ 4% match
Annual 5% Profit-Sharing Bonus

KLM Trucking

CDL-A Truck Driver | No Touch | Dry Van

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,210 - 1,565 Per week

Assigned manual tractors. Dry van trailers. Safety incentives available
Positions are limited. 6 months recent tractor trailer experience required.
Medical, Dental, Vision and Life Insurance. 401K with company match

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!
20+ years experience in dispatching. Abundant Freight
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

Delta Carrier Group, Inc

CDL A OTR Lease Driver / SAP Accepted

Hiring in Wisconsin and 47 other locations
OTR, Regional
2 weeks out
$2,500 Per week

We have OTR COMPANY DRIVER OFFER FOR REEFER - 2023, 2022, 2021 Kenworth T680, Also VOLVO 2020 and 2019 are available
No down payment OR balloon payment. Tons of new trucks available
Reefer truck Driver needs to have at least 1 year recent OTR experience

Best Way Transportation LLC

Owner Operator/Fleet Owners -Flatbed

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

We are professional, agile and our goal is to Find you good paying loads and to keep you moving
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

Dedicated Logistics, Inc

Class A Regional Flatbed Driver Home Weekly

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$83,200 Per year

10-15% of the loads require tarping (4ft tarps).
Hands-Free Headset Reimbursement. Work Boot Reimbursement
Paid Training. Discounts on many events

South Shore Transportation Company

CDL-A Flatbed Truck Driver - Home Weekly

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,800 Per week

Our family business is committed to providing our customers AND our employees with superior service. Join the South Shore family today! No flatbed experience? No problem!
CDL-A flatbed truck driver jobs that GET YOU HOME! Spend quality time at home on the weekends and get steady loads when you join South Shore Transportation! We have a new increased pay package and are offering more benefits for regional CDL-A flatbed runs in!
Great health benefits starting the first of the month after 60 days. Group health, dental, vision, life, short-term disability, prescription drug card, flexible spending account. Assigned late model equipment (Volvos and Freightliners, 100% with auto-shift transmission, and 3000-Watt inverter).

PGT Trucking, Inc.

CDL A Flatbed Company Driver Position

Hiring in Wisconsin and 47 other locations
OTR, Regional
Weekly
$84,000 Per year

Drive for the Best: Company flatbed drivers at PGT Trucking earn an average of $84,000 per year with top performers earning more! Be home every weekend. Drive new 2023 and 2024 International and Peterbilt Tractors, and enjoy excellent benefits.
Home every weekend. New 2023 and 2024 International and Peterbilt Tractors. Weekly pay. Paid Orientation in Blairsville, PA (PGT provides all travel arrangements. Experienced flatbed drivers can seat the first week!
Medical, dental and vision insurance. Company-paid life insurance and long-term disability. 401(k), including 100% match up to 5% gross pay. $5,000 driver referral bonus. Retention bonuses with safety incentives - $6,000 within the first two years

Clean Harbors

Owner Operator-Class A Dry Van

Hiring in Wisconsin and 47 other locations
OTR, Regional
2 weeks out
$4,500 Per week

Health and Safety is our #1 priority and we live it 3-6-5! Positive and safe work environments. Opportunities for growth and development in all the stages of your career.
Ensures that Health and Safety is the number one priority by complying with all safe work practices, policies, and processes and acting safely at all times. Operates tractor-trailer tanker units and other vehicles.
Clean Harbor is an equal-opportunity employer. We do not discriminate against applicants due to race, ancestry, color, sexual orientation, gender identity, national origin, religion, age, physical or mental disability, veteran status, or based on any other federal, state/provincial, or local protected class.

Regional CDL driver jobs in Wisconsin