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 can also help with the registration.

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

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!

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 home most weekends. No forced dispatch

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

Possibility to earn up to 92% of gross per week
Experienced & Dedicated Dispatcher.
$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

$250/week - Dry Van Rental. Get a FREE trailer for 1 month!
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 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

Low company fee 10%. No authority needed. Personal dispatcher with 24/7 support
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.
We're Global Transportation, and we're creating a HUGE buzz among the real heart of the trucking industry: independent owner / operators just like you. In-house brokerage department. Shippers know that we only hire the best drivers, so we get a constant flow of top paying loads.
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

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.
Compliance Confidence: We handle the complexities of driver and vehicle compliance, so you can focus on your core business. Profitability Partner: Sheppard Logistics Group is dedicated to enhancing your bottom line through insightful BEP analysis and cost control strategies.
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

Sutton & Pouncey Transportation is looking for quality, independent, Dry-Van & Reefer, owner operators, carriers and small fleets. We are dispatchers, carrier managers & logistics experts, who specialize in driver/carrier management.
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.
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