Owner Operator CDL Driver Jobs in Illinois May 2026

CDL DNA

Owner Operator - Dedicated Midwest Regional Runs

Hiring in Illinois and 10 other locations
Owner Operator
2 weeks out, 3 weeks out
88% Of gross

We offer to split 88% / 12%, where the fee will cover our dispatch and safety services.
We have a lot of broker connections and book loads before they get to the board.
We are very flexible and will adjust to your liking.

Short HIGH Paying Loads

Direct Freight

Flexibility and full transparency guaranteed

Duka Transportation, Inc.

OTR Flatbed Owner Operators

Hiring in Illinois and 46 other locations
Owner Operator
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

Alpha Express LLC

CDL A Owner Operator | 90% of Gross

Hiring in Illinois and 46 other locations
Owner Operator
Flexible
$30,000 - 35,000 Per month

Pay: $30,000.00 - $35,000.00 per month. Trucking driver type: Owner-operator.
Benefits: Health insurance, Referral program.
We offer Freight in all 48 states! Run the areas you want!

Jim Lawrence Transportation, Inc.

Owner Operators OTR CDL A Truck Driver

Hiring in Illinois and 46 other locations
Owner Operator
Weekly, Flexible
$100,000 - 290,000 Per year

Pay: $100,000.00 - $290,000.00 per year.
Benefits: Dental insurance, Health insurance, Referral program, Vision insurance
Drivers are treated with respect by dispatchers. You're a person, not just a truck number.

Hittman Transport Services, Inc.

Owner Operators CDL A Team Truck Drivers

Hiring in Illinois and 46 other locations
Owner Operator
Daily, Flexible
$10,000 Per week

Hittman Transport Services, Inc. is contracting owner operators.
Teams make up to $10,000 weekly. Quarterly Fuel Discount, plus Discounts at the pump.
Hittman Transport pays for the yearly expenses: tolls, fuel tax, tractor washes...

TPA Cargo Solutions LLC

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

Hiring in Illinois and 46 other locations
Owner Operator
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

Fox Carriers

CDL A Dry Van Semi Truck Owner Operator

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

Experienced & Dedicated Dispatcher.
Cargo and Liability Insurance. Fuel Cards
$2000 sign-on (after 6 months) and driver referral bonuses;

Pelts Xpress

CDL A Owner Operator | Regional Runs

Hiring in Illinois and 46 other locations
Owner Operator
Flexible
88% Of gross

88% of gross revenue. Up to $0.40 fuel discount (100% to the owner)
Flexible dispatch adjusted to your preference. Solo & Team loads
Assistance with Plates & Registration. Warm and welcoming team

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 Illinois and 47 other locations
Owner Operator
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!

Empire National Inc.

OTR Dry Van Owner Operator

Hiring in Illinois and 47 other locations
Owner Operator
Flexible
90% Of gross

Empire National Inc Owner Operators get 90% of the gross rate On average, our owner operators make $6-8 k + gross weekly!
No forced dispatch - 100% Freedom to run where you want to
Fuel cards available with NASTC Discounts for TA and Petro

Global Transportation LLC

Hiring Owner Operators - 27 Reefers Left

Hiring in Illinois and 47 other locations
Owner Operator
Flexible
88% Of gross

Truck Owner / Operators: Get High-Grossing Loads 24/7. Real people. Real Support. Gross $10k-$12k a week. Wouldn't that be a load off your shoulders? Proven success rate. Brokers and shippers KNOW they can trust Global Transportation to deliver, so we're #1 on their go-to list.
Superb dispatcher training system for getting best rates from a load board. Our dispatchers are ON THE JOB 24/7 and negotiating hard for you. Highest weekly income and return on your truck investment.
Our Owner Operators gross between $10k - $12k per week and keep 88% of that. Our exceptional driver support is what makes us #1. Want to hear from REAL drivers about why they LOVE Global Transportation.

Sheppard Logistics Group

Owner Operator/ Fleet Owner - Dry Van

Hiring in Illinois and 47 other locations
Owner Operator
Weekly
$4,000 Per week

Sheppard Logistics Group is a trusted leader in freight dispatching and compliance services for owner-operators, fleet owners, and trucking companies. TMS Excellence: Our TMS simplifies your logistics by providing a single platform for communication, tracking, and reporting.
With a relentless commitment to excellence, we handle all day-to-day freight dispatching operations, providing 24/7 dispatch support and ensuring compliance with driver regulations and vehicle maintenance management.
Market Updates: We provide valuable insights into market conditions, rate trends, and industry developments, in addition to personalized business operation updates, tailored to individual clients, to address their specific needs and goals.

S &P Dispatching

Reefer Owner Operator/Small Fleet Owners

Hiring in Illinois and 47 other locations
Owner Operator
Weekly
$6,100 Per week

We partner with you to help relieve the stress the trucking the trucking business can bring. We are lane mindset oriented, focused on finding and putting our carriers on the highest paying, most profitable lanes.
We provide break-even point analysis, free of charge, so you can keep track of your business easily and every load run, to ensure that you are making a profit.
Break-even analysis for your business to make sure you are running in the profit zone. 24/7 Dispatching service. Carrier packet setup. Compliance assistance & management. Lane specific placement to ensure the best rates for you

S &P Dispatching

Dry Van Owner Operator/Small Fleet Owners

Hiring in Illinois and 47 other locations
Owner Operator
Weekly
$6,100 Per week

S&P alleviates the pressure and stress of searching, booking and dispatching loads, as well as all the paperwork and on-boarding that comes with that, so you and your drivers can focus on safety and making more money.
We focus on low deadhead, efficient loads on profitable lanes that keep you consistently in a good and profitable position as a business. We can/will handle all factoring, as well as any issues with your loads that are within our ability.
Break-even analysis for your business to make sure you are running in the profit zone. 24/7 Dispatching service. Carrier packet setup. Compliance assistance & management. Lane specific placement to ensure the best rates for you

Soloymi Inc.

Owner Operators Dry Van needed 88%

Hiring in Illinois and 47 other locations
Owner Operator
Flexible
88% Of gross

Hello fellow Owner Operators, please read the info below and call/text/apply if you like what you see. We do not have forced dispatch, but if you try to choose loads at this time that will bring no good.
You probably won't make a fortune in this market, but if you make your pickups and deliveries on time, we will keep you running every day.
We can get $2.00-$2.20 per mile at this time. Doing more complicated loads can bring you a little bit better average. We use Motive/Keeptruckin log books.

Owner Operator CDL driver jobs in Illinois