1099 CDL Driver Jobs in Illinois September 2025

CDL DNA

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

Hiring in Illinois 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

C1 Transportation Inc

CDL A Flatbed OTR Driver

Hiring in Illinois and 45 other locations
Flexible
30% Of gross

2021-2025 Volvo, Freightliner, International and Kenworth's
Direct Deposit weekly, payments should be received by Friday each week.
8 driver maximum per one dispatcher, which allows our dispatchers to pre-plan loads for you.

Steady Weekly Paycheck

Paid Orientation

Pre-planned Trips

CDL DNA

CDL A - Company Driver - 1099 - Flat Rate

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

W2 and 1099 Positions Available

Professional Work Environment

Fully Loaded Trucks

Ashley Distribution Services LTD

Regional OTR CDL-A Truck Driver | $81,000/year

Hiring in Illinois and 46 other locations
Weekly
$81,000 Per year

Top 25% of drivers earn $81,000 annually. Regional routes. Regular 34-hour resets at home. No-touch freight.
Mix of live load/unload and drop and hook accounts. Consistent, high weekly miles. Excellent, premium equipment.
Generous benefits package: Can add up to an additional 27% on top of your base salary! Job stability.

CDL DNA

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

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

Lease Rental or Lease Purchase program for experienced drivers
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.

$0 Down, No Credit check

Only for experienced drivers

All charges and trailer included in %

Duka Transportation, Inc.

OTR Flatbed Owner Operators

Hiring in Illinois 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

Quality Wheels Inc

CDL Company Driver 1099 OTR

Hiring in Illinois and 19 other locations
2 weeks out
$0.60 Per mile
/
27% Of gross

We pay $0.60 per mile OR 27% from gross - your choice
Home Time: 2 Weeks OTR and 2 Days home - 4 weeks on the road/5 days home
Weekly Settlements are on Thursdays with direct deposit

Make $1,800 - $2,000 per week

Paid Time Off

Automatic & Manual Trucks

CDL DNA

CDL A Independent Contractor 1099 | 70-75 CPM

Hiring in Illinois 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 Illinois 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 Team Drivers for Amazon Loads - Flat Rate

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

Most of the loads are DROP-N-HOOK
We have a great variety of trucks from 2022 to 2024 year models
We can give you north of 6,000 mi per week

$1,900 Weekly Flat Rate

Drop & Hook Loads

Team Matching Available

CDL DNA

CDL A Strong Company Driver 1099 - Drop & Hook

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

Most of the loads are DROP-N-HOOK
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

Only For Strong Solo Drivers

$2,500 - $3,200 Per Week

Drop & Hook Loads

CDL DNA

CDL A Reefer Truck Driver - Up to 31%

Hiring in Illinois 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

Transurfing Inc

CDL A Reefer & Dry van Company Driver OTR

Hiring in Illinois and 46 other locations
3 weeks out
$0.63 - 0.65 Per mile
/
28 - 30% Of gross

We have a lot of customer freight and need professional, responsible and safe drivers to help us move it
If you are looking for a consistent job, you are welcome to apply
Operating in Midwest and West Coast

Only For Safe and Responsible Drivers

Great New Trucks & Equipment

Consistent Direct Freight

Fox Carriers

Class A Dry Van Owner Operator

Hiring in Illinois and 47 other locations
Flexible
92% Of gross

You choose what time to work. 24/7 Driver Support
Possibility to earn up to 92% of gross per week
Lots of direct customers and dedicated lanes

Jahany Transportation Logistics LLC.

CDL A Dry van Owner Operator Hazmat Required

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

90/10 Split: You Keep the Majority of Your Earnings!
Trailer Rent: $250 per week (if you don't own a trailer)
Essential Requirements: Valid Plates & Regs, Hazmat Endorsement

1099 CDL driver jobs in Illinois