Regional CDL Driver Jobs in Wisconsin March 2026

Industrial Cargo Logistics Inc

Owners-Operators - Flatbed/Step Deck/Conestoga

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

A+ Insurance with $250k of coverage
Former drivers dispatch team
Best rates negotiation. Reputable brokers. Trip planning.

A+ Insurance with $250k coverage

USA Based Dispatchers

Direct Freight

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

Heartland Express

CDL-A Regional Truck Driver | Dry Van No Touch

Hiring in Wisconsin and 46 other locations
Regional
Weekly
$67,000 - 94,000 Per year

$67,000 $94,000 depending on location.
Dry Van Freight No Touch, Drop and Hook.
Health, dental, vision and life insurance.

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

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.
Supplemental pay types: Bonus opportunities, Detention pay, Safety bonus

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

Pay: $0.60c/ per mile. Miles Per Week: 2500-3500 mi
Equipment: 2020-2024 automatic Freightliner Cascadia
Pets Friendly. APU, Fridge, Power Inverter in trucks

Dedicated Local and Regional Runs

Jahany Transportation Logistics LLC.

CDL A Dry van Owner Operator Hazmat Required

Hiring in Wisconsin and 47 other locations
Regional
Weekly
$8,000 - 12,000 Per week

Trailer Rent: $250 per week (if you don't own a trailer)
Save on fuel with our fuel card, offering discounts of up to 60 cents per gallon
Essential Requirements: Valid Plates & Regs, Hazmat Endorsement

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

100 %No Touch Freight
Mostly Drop & Hook
Steady customer interaction on daily bases

Indianapolis Fruit Company

Reefer Truck Driver - CDLA - Indianapolis, IN

Hiring in Wisconsin and 46 other locations
Regional
2 weeks out
$29 Per hour

Scheduled annual increases
Shifts typically start between 12am – 5am. Typical workday is 12-14 hour per day
Routes can have 3-10 stops per day

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

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.
Minimum inside dimensions of the cargo area 100x50x50 inches (L x W x H).
Clean and tidy vans are preferred - no debris, spots, dents, etc.

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)
20+ years experience in dispatching. Abundant Freight

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

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!

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.

Clean Harbors

Owner Operator-Class A Dry Van

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

$7500 Sign-on Bonus Available. Clean Harbors San Jose, CA location is looking for an OTR Class A Dry Van Driver to join their safety-conscious team! Average annual driver salary: $250K+/yr
Our Class A Driver is responsible for running a route from San Jose, CA to Salt Lake City, UT, running 2800 miles a week. Primarily driving tractor/trailer combos, this position requires traveling away from home for up to 12-14 days at a time.
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