1099 CDL Driver Jobs in Wisconsin August 2026

CDL DNA

CDL A HazMat Reefer Driver - Up to $0.75/mile

Hiring in Wisconsin and 46 other locations
3 weeks out
$0.65 - 0.75 Per mile

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TOP PAY FOR QUALIFIED DRIVERS

CONTRACTED STABLE FREIGHT

BRAND NEW REEFER TRAILERS

CDL DNA

OTR 1099 Company Driver - $0.65 CPM ALL MILES

Hiring in Wisconsin and 22 other locations
2 weeks out
$0.65 Per mile

Top equipment (Volvo, Freightliner, Kenworth, Pete)
We pay every Friday for all loads delivered up until Monday of the same week.
Pets and passengers are always welcome

Avoid 34h restarts

Consistent flow of loads

Friendly and professional office team

A&V Cargo Inc

Small Fleet Is Hiring A Company Driver

Hiring in Wisconsin and 46 other locations
2 weeks out
30% Of gross
/
$0.60 Per mile

Small fleet is hiring. Flatbed trailer - we will haul everything that will fit on a 53ft flatbed.
Running all over Midwest, South and South East
Forwarding all rate confirmations. We offer a respectful and fair treatment, on-time salary and all around support!

Owner Operated Small Company

Full Transparency

CRST The Transportation Solution Inc

CDL-A Flatbed Owner Operator | Solo or Team

Hiring in Wisconsin and 46 other locations
Flexible
75% Of gross

Owner Operator Options. Solo or Team positions. Paid Up to 75% of the Gross revenue of each load. Weekly Payroll.
Flatbed securement training program available. Fleet Manager Assistance Option or Run On Your Own.
Manual and Automatic transmissions. Variety of Trailer Rental Options. Retention Bonuses available. Pick your Own Loads.

Eos Inc.

OTR Solo or Team CDL-A Truck Driver | Drop & Hook No-touch

Hiring in Wisconsin and 46 other locations
2 weeks out
$0.60 Per mile

Earn $80,000 - $130,000 per year. Up to 60 CPM based on experience. Home every 2 weeks. Average 2,800-3,200 miles per week.
Running area: Midwest Mid, Atlantic, and Southeast, PA, very little NJ, no NYC. Mostly drop & hook no-touch freight. Solo or Team driver.
Our fleet is constructed of 2021-2024 Automatic Freightliners, Volvos, Macks, KWs, INTLs, and Peterbilt. Paid 2-day Orientation.

CDL DNA

CDL A - Company Driver - 1099 - Flat Rate

Hiring in Wisconsin and 25 other locations
2 weeks out, 3 weeks out
$0.63 - 0.67 Per mile
/
$290 Per day

As a Company Driver (1099), you will enjoy a stable work and predictable paycheck every week.
Depending on your location, you will be able to return home every 2-3 weeks.
Real Trucking is a highly reputable carrier with a fleet of over 300 trucks.

W2 and 1099 Positions Available

Professional Work Environment

Fully Loaded Trucks

Royal Trucking Company

Lease CDL A OTR Truck Driver

Hiring in Wisconsin and 46 other locations
Flexible
$78,000 - 100,000 Per year

Dry Van Trainees : Up to $58K Year. Dry Van Experienced Drivers : $72K-$78K Yearly.
Flatbed Trainees : $61K Year. Flatbed Experienced Drivers : $85K-$100K Yearly.
Competitive Pay. Excellent Benefits. Consistent Freight.

Risinger Brothers Transfer, Inc.

CDL-A Lease Purchase | Solo Gross $4K-6K/Weekly

Hiring in Wisconsin and 46 other locations
Flexible
$1.22 Per mile

Lease purchase program. Paid toll fees. Paid toll fees.
$1.22 per mile + Current Fuel Surchage Rate on all loaded and empty dispatched miles.
Prioritized Home Time. Weekly Settlements. Company Paid Tolls & Scales.

Duka Transportation, Inc.

OTR Flatbed Owner Operators

Hiring in Wisconsin and 46 other locations
Flexible
$300,000 - 360,000 Per year

Top 30% of our drivers earn $320,000 or more gross annually
Save on the fuel pumps - Company fuel cards with discount
Be home weekly or every other week

GN GROUP INC

OTR CDL A Reffer Driver | 70CPM

Hiring in Wisconsin and 46 other locations
Flexible
$0.60 - 0.70 Per mile

GN GROUP INC experienced REEFER transportation company is looking for safe CDL class A truck drivers!
Solo Drivers starting at $0.60-$0.70 Cent Per mile. Pay: $1,500.00 - $2,800.00 per week.
CDL - Class A License. Verifiable 2 years of recent OTR Experience.

Just Trucking Services

Class A Independent Contractors 1099

Hiring in Wisconsin and 46 other locations
2 weeks out
$2,200 - 2,400 Per week

Steady weekly take home $
At least 3,000 weekly miles. 2-3 out weeks & 3-4 days at home (flexible)
Welcome Independent contractors to join our small family owned company

Small Family Owned Fleet

Flexible Dispatch

$2,200+ per week

CDL DNA

CDL A Independent Contractor 1099 | 70-75 CPM

Hiring in Wisconsin and 46 other locations
3 weeks out
$0.70 - 0.75 Per mile
/
30 - 33% Of gross

You will be driving a 2021-2024 truck
Cash advances are available to you as long as you are under the load
Take home around $2,100-$2,500

TPA Cargo Solutions LLC

CDL A Owner Operator | $4,000-5,000 take-home

Hiring in Wisconsin and 46 other locations
Flexible
85% Of gross

Personal dispatcher. No forced dispatch
Drop & hook, live load & live unload loads
No touch freight. 24/7 support. Consistent back to back loads

Consistent Back To Back Loads

$4,000-$5,000 Weekly Take-home

Professional No Forced Dispatch

CDL DNA

CDL A Team Drivers for Amazon Loads - Flat Rate

Hiring in Wisconsin and 46 other locations
4 weeks out
$1,900 Per week
/
$0.75 Per mile

Most of the loads are DROP-N-HOOK
Drivers that are willing to run make $2,500 - $3,200 per week
We have a great variety of trucks from 2022 to 2024 year models

$1,900 Weekly Flat Rate

Drop & Hook Loads

Team Matching Available

CDL DNA

CDL A Reefer Truck Driver - Up to 31%

Hiring in Wisconsin and 45 other locations
3 weeks out
27 - 31% Of gross

We have one of the most experienced dispatchers in the industry
As a Company Driver, you can expect exceptional service , support and communication
Drivers who are ready to stay on a road for long and drive hard can get 31% of gross

$2,000 - $2,500 Weekly Take-home

Company With Great Reputation

Professional and Friendly Environment

1099 CDL driver jobs in Wisconsin