1099 CDL Driver Jobs in Wisconsin February 2026

Hugo Hunter Inc

CDL-A Owner Operator | 90% of Load Gross

Hiring in Wisconsin and 46 other locations
Flexible
90% Of gross

90 Percent of Gross Pay! 24/7/365 Dispatch and Road Service. Weekly Pay Via Direct Deposit.
100% Fuel Advance with Competitive Fuel Discounts. Premium Health Benefits Package.
Reefer, Open-Deck, And Dry van Trailer Rental for as low as $250 per week. Full Service.

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.
We provide you with a fully loaded 2021-2024 Freightliner Cascadia equipped with a refrigerator, microwave, inverter, APU, mattress, and tablet.
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

CDL DNA

CDL A - Lease Purchase & Rental Program - $0 Down

Hiring in Wisconsin and 46 other locations
2 weeks out
78 - 80% Of gross

Trucks are 2022-2023 Freightliners with 100k-400k miles
Dispatchers will try to maximise your weekly gross working with the spot market and their direct contracts with brokers.
You only pay for truck, fuel, and tolls.

$0 Down, No Credit check

Only for experienced drivers

All charges and trailer included in %

Motherland Investments

CDL A - OTR Dry van Company Driver

Hiring in Wisconsin and 4 other locations
2 weeks out
$0.65 - 0.70 Per mile

We're looking for responsible and experienced drivers to join our team.
This is an OTR position for drivers who are willing to drive.
We guarantee at least 3,000mi weekly and more if you desire.

No check hold

New equipment

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.
$2,500 Solo Sign On Bonus - $5K Team Sign On Bonus.
Prioritized Home Time. Weekly Settlements. Company Paid Tolls & Scales.

Alpha Express LLC

CDL A Owner Operator | 90% of Gross

Hiring in Wisconsin and 46 other locations
Flexible
$30,000 - 35,000 Per month

Have your own Semi-Truck? Owner Operator Truck Drivers earn 90% of Load Gross!
Pay: $30,000.00 - $35,000.00 per month. Trucking driver type: Owner-operator.
We offer Freight in all 48 states! Run the areas you want!

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.

CDL DNA

CDL A OTR Company Driver - up to $2,600/week

Hiring in Wisconsin and 46 other locations
3 weeks out
$0.62 - 0.65 Per mile
/
27% Of gross

We deliver all over the country. Mix of direct and load board freight
3,500-4,000 miles weekly. $8,000-10,000 weekly gross
95% of our drivers make $0.65/mile and take home $2,200 - $2,600 every week.

3,500 - 4,000 miles guarantee

Experienced dedicated dispatchers

Steady weekly paycheck

AAA Transit Group LLC

CDL A Owner Operator St Louis and Midwest region

Hiring in Wisconsin and 11 other locations
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.

CDL DNA

CDL A OTR Dedicated Team Drivers - 80 CPM

Hiring in Wisconsin and 43 other locations
3 weeks out
$4,000 - 4,600 Per week
/
$0.75 Per mile

Dedicated round trips all over the country
2023-2024 Kenworth, Peterbilts trucks
You don't have to live near the dedicated lane, as we can find you a load from board to get you home.

$2,000 - $2,300 per driver flat

Dedicated Lanes

2023-2024 Trucks

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
No touch freight. 24/7 support. Consistent back to back loads
Average owner operator gets a paycheck of $4,000-$5,000 per week after all expenses

Consistent Back To Back Loads

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

Professional No Forced Dispatch

CDL DNA

CDL A Strong Company Driver 1099 - Drop & Hook

Hiring in Wisconsin and 46 other locations
4 weeks out
$0.65 Per mile

We are looking specifically for drivers who can run a lot of miles and stay out for 4 weeks at the time
We have a great variety of trucks from 2022 to 2024 year models
Drivers that are willing to run make $2,500 - $3,200 per week

Only For Strong Solo Drivers

$2,500 - $3,200 Per Week

Drop & Hook Loads

Sinbex Dispatch LLC

Owner Operators & Fleet Owners | Power Only

Hiring in Wisconsin and 47 other locations
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

I&A LOGISTICS LLC

CDL A Owner Operator

Hiring in Wisconsin and 47 other locations
Flexible
88% Of gross

For driver with TWIC card we work with UIIA, so the payment is much more higher
Working with VIP brokers. Our drivers are doing up to 9 to 12k.
Company fee 12% from total gross. Available amazon load board with 100% performance

Odysseia

CDL C Sprinter Van / Cargo VanOwner Operator

Hiring in Wisconsin and 47 other locations
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.

1099 CDL driver jobs in Wisconsin