Regional CDL Driver Jobs in Wisconsin May 2026

Industrial Cargo Logistics Inc

Owners-Operators - Flatbed/Step Deck/Conestoga

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

Former drivers dispatch team
Main load and partials, we don't let the truck travel half empty, any available space on the trailer is used.
Best rates negotiation. Reputable brokers. Trip planning.

A+ Insurance with $250k coverage

USA Based Dispatchers

Direct Freight

NFI Interactive Logistics LLC

Midwest Dedicated CDL-A Truck Driver | $1,500/wk

Hiring in Wisconsin and 11 other locations
Local, Regional
Weekly
$1,500 Per week

Average Pay: $1,500/wk. Schedule: On call/flex load out times (afternoons); Tues/Sat off.
Immediate Benefits - Health, Dental, Vision, Rx. 401(k) with Match. Quarterly & Annual Safety Bonus.
Average Tractor Age Less Than 2.5 Years. Collision Mitigation Systems. 24 / 7 / 365 Driver Support.

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

R and J Trucking, Inc.

CDL A Truck Driver $2,500 per week

Hiring in Wisconsin and 46 other locations
Regional
Weekly
$1,200 - 2,500 Per week

This position will have you home every week and does not require a tank endorsement!
R&J offers excellent wages, benefits (after 60 days,) 401-K, Vacations, and Bonuses.
The average gross pay has been around $1,800 per week with many drivers exceeding that.

Sinbex Dispatch LLC

Owner Operators & Fleet Owners | Power Only

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$5,000 - 10,000 Per week

Transparency is key, and the moto we live by
Load booking, Rate negotiating, Signing rate confirmations and broker-carrier packets
Fixed commission fee. Welcome small fleet owners

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
2800 weekly average miles

Show ME Transportation

CDL A Driver - Dry Van - Home Weekly

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$0.70 Per mile

Home weekly for reset
Mostly drop and hook - some live unload
Full benefits - Medical, Dental, Vision, 401k, Life, etc.

Salt City Trucking

CDL A REGIONAL / OVER THE ROAD Driver

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$1,200 - 1,500 Per week

Full Benefits. Medical, Dental, Vision & Retirement! Paid Orientation
Year round freight, consistent miles! WE NEVER SLOW DOWN! Lots of money to be made!
Weekly Pay. Unlimited Cash Referral Program. Dedicated client/company

Pelts Xpress

CDL A Owner Operator | Regional Runs

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

88% of gross revenue. Up to $0.40 fuel discount (100% to the owner)
20+ years experience in dispatching. Abundant Freight
Flexible dispatch adjusted to your preference. Solo & Team loads

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

OPERATING MOSTLY MIX OF MIDWEST, NORTH EAST, AND SOUTHERN STATES.
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
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

New, leased trucks! 2021-2023 FREIGHTLINER CASCADIAS
Freight Type : Flatbed freight; steel coils, steel sheets, steel bars, etc.
Bonuses available: Attendance ($185/quarterly), Safety($100/quarterly), Yearly Retention($1000/year)

Empire Express

CDL-A REGIONAL FLATBED DRIVER

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$75,000 - 100,000 Per year

Customizable insurance options. Optional dental and vision coverage
Ask about our free medical plan!
We would love to have you join the Empire Family

Beemac Trucking

Class A Owner Operators - Flatbed

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$2,000 - 3,000 Per week

We are currently looking for Class A CDL Owner Operators. Owner Operator company. Dry Van will Gross $5,000-$6,000 a Week. Flatbed will Gross $6,000-$8,000 a Week.
Home Every Weekend or you can stay out multiple weeks. Company Paid Liability and Cargo Insurance. No IFTA Charges. Insurance Program. 100% Non-Forced Dispatch.
National Fuel Discount Program ( Average $0.50 to $0.80 off ). Tag Program. Trailer Rental Program. FSC. Must Have at least 2 Years of CDL A Experience.

CRST The Transportation Solution Inc

CDL A Lease Purchase Flatbed Truck Driver

Hiring in Wisconsin and 47 other locations
OTR, Regional
Flexible
75% Of gross

CRST Flatbed Solutions is one of the nation’s largest transportation companies, providing total transportation solutions and comprehensive logistics services to customers all over North America.
We are looking for independent contractors (Lease Purchase) that would like to join our fleet that has been a leader in the flatbed marketplace since 1919. Lease Purchase Options.
Solo or Team positions. Paid Up to 75% of the Gross revenue of each load. Ask your recruiter on the weekly Rate Per Mile. Retention Bonuses available. Pick your Own Loads.

Regional CDL driver jobs in Wisconsin