cdl owner operator jobs in Chicago

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10,000 cdl owner operator job listings in United States. Find daily updated positions from leading job boards.


  • Chicago, IL, United States ARL Network Full-time

    Job Description Job Description Job Requirements: - At least 23 years of age - 2 years verifiable Class A CDL tractor-trailer experience, including 6 months with the trailer type being hauled - Current DOT physical - Not prohibited in the FMCSA Drug & Alcohol Clearinghouse - No more than 100 CSA points - Tractor model year 2000 or newer - Must meet ARL...


  • Chicago, IL, United States QFS Owner-Operators Full-time

    QFS Transportation | Greenville, Ohio OWNER OPERATORS WANTED — MULTIPLE OTR POSITIONS AVAILABLE! QFS Transportation is growing, and we’re looking for experienced CDL-A Owner Operators to join our team! If you own your truck and are looking for consistent contracted freight, strong earning potential, fuel discounts, and an established carrier...


  • Chicago, IL, United States Hudd Transportation Full-time

    CDL-A Owner Operators – Local, Regional & Intermodal Opportunities Multiple Locations | Earn Up to $312,000 Annually | Home-Daily Opportunities | NEW Incentives Available HUDD Transportation is hiring experienced CDL-A Owner Operators for local, regional, port, rail, and intermodal opportunities across...


  • Chicago, IL, United States MAERSK Full-time $156,000 - $312,000

    $156,000 - $312,000/year earning potentialLocal, home daily positionNew performance incentivesAll empty and loaded miles paidPre-dispatched the day beforeDriver-focused supportRequirements:Must possess a valid Class A commercial driver’s license (CDL A)Some port or intermodal experienceMust operate a well-maintained 2014 tractor or newer that meets DOT...


  • Chicago, IL, United States STG Logistics Full-time

    Owner-Operators Needed for Intermodal & Drayage Freight STG Drayage is growing its intermodal and drayage network and looking to contract with experienced CDL-A Owner-Operators in surrounding port and rail markets. If you’re an owner-operator with your own truck looking for consistent container freight, competitive rates, and a...


  • Chicago, IL, United States Atom Logistics Inc Full-time

    BOX TRUCK OWNER-OPERATORS NEEDED - OTR | GROSS $6,500-$8,500 WEEKLYWe are looking for reliable Non-CDL Box Truck Owner-Operators ready to run consistent OTR freight across the continental United States.PAY & BENEFITSAverage weekly gross: $6,500-$8,500Keep 90% of gross revenueOnly 10% service feeOnboarding completed in as little as one dayFuel card with...


  • Chicago, IL, United States ContainerPort Group Full-time

    CDL-A Owner Operators -Home Daily Intermodal Freight | High Earning Potential We’re contracting CDL-A Owner Operators for local intermodal freight with ContainerPort Group, one of the nation’s top 10 drayage carriers with over 55 years of proven success. If you’re looking for consistent...


  • Chicago, IL, United States Trimac Full-time

    Overview Trimac isn't just a transportation company; we’re a safety-driven team powered by 80 years of legacy. Our team is proud to safely deliver products that improve people’s lives across North America. We offer our drivers a wide range of opportunities, including transporting chemicals, handling dry and liquid bulk goods and providing specialized...


  • Chicago, IL, United States ContainerPort Full-time $200,000 - $273,000

    Owner operators, put your truck to work with a top 10 drayage carrier backed by 55 years of success. If you want consistent freight, strong weekly settlements, and real support - let’s roll!Pay and Compensation:Weekly settlementsHouston, Texas:$4,500/week$1,500 Sign on BonusWIC Required$7,000/week$1,500 Sign on BonusTWIC RequiredNorfolk, VA:$5,400/...


  • East Chicago, IN, United States Forward Full-time

    Partnering with CDL-A Intermodal Owner-Operators in Cudahy, WI, and Chicago, IL - Estimated Yearly Earnings: $130k - $156k / Year Looking for an intermodal career with great weekly pay, a dependable schedule, and less hassle? Forward is partnering with Class A CDL Owner-Operators in the Cudahy, WI area to run local and regional intermodal routes between...


  • Chicago, IL, United States H&H Recruiting Full-time

    Independent Contractor Opportunity$10,000 Contract Signing Incentive | No Forced Dispatch | Weekly SettlementsOperating Area: Primarily east of I-35Take Control of Your Business and Your Earnings!Seeking experienced CDL-A Owner Operators ready to grow their businesses with access to one of the nation's largest freight networks.Enjoy the freedom to choose...


  • Chicago, IL, United States Unknown Full-time

    Looking for a Class A CDL Owner Operator job with consistent freight, excellent pay, and a company that values its drivers? Join a family-owned trucking company, where you're treated like a partner - not a truck number. We believe experienced owner operators deserve respect, honest communication, and reliable freight. That's why our driver retention is among...


  • Chicago, IL, United States 2 AM Group INC Full-time

    Job DescriptionJob DescriptionPay: $9,000.00 - $17,000.00 per weekJob description:Drive With 2AM Group INC – Built by Drivers, For DriversAt 2AM Group INC, we’re not a big corporation — we’re a family-owned company. Every driver represents our personal reputation, so honesty, fairness, and respect are the foundation of how we do business.We know what...


  • chicago, il, United States Clark Transfer Full-time

    Job DescriptionJob DescriptionJoin an owner-operator family with 75 years of experience moving time sensitive live entertainment.Great Work:Moving Broadway shows and other live entertainmentYear-round workNo touch policyHigher Compensation on Fewer Miles!Most solo drivers earn $175,000 to $225,000+ annually on less than 85,000 miles.Guaranteed Average Weekly...


  • Chicago, IL, United States HUDD TRANSPORTATION Full-time

    Job DescriptionSkills, Experience, Qualifications, If you have the right match for this opportunity, then make sure to apply today.Chicago / Elwood, IL | Home Daily | Local & Regional Rail Freight$156K–$312K+ Annual Earning PotentialHUDD Transportation is looking for experienced CDL-A owner operators/small fleet owners for steady rail freight out of the...


  • Chicago, IL, United States CDL Training Guide Full-time

    Independent Contractors and Small Fleet Owners can expect: $156K–$312K+ Annual Earning Potential Typically 3–5 moves per day Home daily lanes All empty and loaded miles paid Pre-dispatched freight 80% drop-and-hook freight Detention pay available Weekend work available 7-day office support Requirements: Valid Class A CDL Own tractor and active...


  • Chicago, IL, United States CDL scan Full-time

    CDL scan is seeking an owner-operator with a Class A CDL to join a family-owned trucking team. You’ll work as a partner, handling consistent freight from direct shippers and enjoying reliable weekly or monthly payments with a strong emphasis on respect and honest communication.Top performers can gross $450,000+ annually, with weekly direct deposits and...


  • Chicago, IL, United States MAERSK Full-time $156,000 - $312,000

    MAERSK is seeking drivers for a local, home daily position offering strong earning potential and new performance incentives. You will be pre-dispatched the day before, and all empty and loaded miles are paid for, with driver-focused support to help you succeed.Qualified candidates must hold a valid CDL A, have intermodal experience, meet DOT safety...


  • Chicago, IL, United States ArcBest Full-time

    ArcBest Corporation is seeking owner-operators to run under our authority with full control of their business. You’ll select loads, get access to our load board and expedited solutions, and enjoy 24/7 driver support. Weekly settlements and a $5,000 sign-on bonus for solo truck owners are part of our attractors. Maintain your own schedule, work as an...


  • Chicago, IL, United States Lostroqueros Full-time

    Hudd Transportation is looking for experienced independent contractors and small fleet owners for steady rail freight out of the Chicago/Elwood market. Run 20–30 moves per week with home-daily lanes, pre-dispatched freight, and a mix of local and regional opportunities. NEW performance incentives are here for Independent Contractors! Ask a recruiter for...