Owner/operator jobs in Winnetka, IL - 262 jobs

Dues-paying membership in Service Employees International Union Local 73 is a condition of employment. Compensation: $22.28 per hour Essential Duties and Responsibilities Drives CJE vehicles to safely transport clients and other designated passengers to and from designated destinations observing all state traffic laws and Agency rules and regulations in accordance with pre-arranged schedule. Properly and safely operates all vehicle equipment including, but not limited to, lift, fire extinguisher, and emergency equipment. Must be physically able to safely operate a vehicle under varied environmental conditions (such as daylight/evening hours, wet/slippery/iced streets, windy) at all times ensuring the safety and wellbeing of the passengers. Must be able to properly secure passengers, including those passengers with assistive devices such as various wheelchair restraints. Must be able to lift and transport box(es) of equipment (such as safety restraints) and other packages and/or materials. Must be able to assist all passengers on/off the vehicle and transfer client's shopping bags on/off vehicles. Must have physical ability, coordination, and mobility to safely and efficiently accompany and assist passengers with various capabilities at all times ensuring the safety and well-being of the passenger. Must be able to safely and properly secure all clients within the vehicle for transport. Must be able to communicate with, understand, and respond to client population and office staff. Must be conversant and aware of the special needs of the client/passenger in order to ensure that clients/passengers feel safe, secure, and comfortable and are treated with consideration, warmth, personal attention and exemplary customer service. Maintains accurate and current records including but not limited to daily schedules, daily/monthly mileage, vehicle inspections forms, client sign-in sheets and incident/accident reports. Must be able to execute written documents on prescribed forms and in accordance with Agency/State regulations. Conveys to Management relevant information about clients and passengers. Attends department meetings and participates in the transportation process. Attends additional meetings as assigned by Management. Must have ability to communicate using telephone, including instances when assistance may not be available. Maintains and wears uniform in compliance with company policy. Maintains vehicles in clean, orderly, safe condition and reports to management in a timely manner any change in vehicle status and/or need for mechanical repair, within established guidelines. Must be able to properly identify, understand, and safely utilize cleaning supplies and equipment for purposes of sweeping, wiping interior surfaces, sanitizing, and picking up and disposing of litter on vehicles. Transports agency staff on agency business. Education and/or Experience High School Diploma or GED. Paratransit experience preferred but not required. Must be at least 21 years of age. Must have a valid State of Illinois driver's license. Must meet the requirements of the Agency's Driver Evaluation Policy as certified by the Secretary of State's Office (MVR check). Must maintain appropriate driving record during employment as defined by the Agency's Driver Evaluation Policy. Must meet all approval requirements of the agency responsible for insuring CJE vehicles. Must comply with Department of Transportation requirements for physical examination upon hire. Pursuant to state requirement, may be required to furnish a record of a physical examination within six (6) months prior to assignment on the job with recertification if a communicable disease has been contracted after the initial examination. Must comply with CJE policies, rules, procedures, and regulations issued by the Federal Highway Administration regarding drug and alcohol testing. Knowledge of service area preferred. Physical Conditions The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions. Must be able to lift and transport box(es) of equipment (such as safety restraints) weighing up to 20 lbs. and other packages and/or materials including assistive devices weighing up to 40 lbs. Requires unaided lifting and transferring, exerting force up to 30 lbs. frequently and up to 40 lbs. occasionally. Must have physical coordination, dexterity & flexibility. Requires sitting for long periods of time. Must be able to consistently and effectively perform multiple tasks simultaneously at and/or above minimum acceptable performance standards under stressful situations. Must have physical mobility and ability to communicate effectively. Requires bending, pushing, pulling, stretching to positions above and below shoulder height, and aided and unaided lifting. Must be able to safely lift and operate assistive devices and equipment. CJE SeniorLife is an equal opportunity employer #CJESL11 Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

Logistix Services Inc Drive with Us as an Owner-Operator! Maximize Your Earnings with Competitive Rates and Full Support! Owner-Operator Truck Driver Type: Full-Time Why Partner with Us? Competitive Earnings: Weekly gross potential of $5,500-$8,000 on 3,000 miles (solo drivers); team drivers can earn $7,500-$9,000 weekly. No Forced Dispatch: Drive on your own terms with full flexibility. 90% No-Touch Freight: Focus on the road without unnecessary hassle. Pet-Friendly Policy: Bring your furry companion along for the ride! Fuel Discounts: Save $0.10 per gallon at major truck stops. Full Support: 24/7 dispatch, safety, ELD, accounting, and fleet support. Reliable Payments: Direct deposit every Friday for the previous week's loads. Dedicated Growth: Whether you operate under your own authority or ours, we ensure your company stays compliant, grows steadily, and maintains a strong safety score for a secure future. Working Options & Fees Option 1: Operating Under Your Own Authority 12% Dispatch Service Fee $50 I-Pass (weekly) $17.65 Pre-Pass (weekly) Full dispatch and back-office support to grow your company, keep you compliant and ensure your safety score remains strong. Option 2: Operating Under Company Authority 15% Dispatch and Factoring Service Fee $250 weekly for cargo insurance and general liability (provided by us). ESCROW: $250 weekly for the first 10 weeks (refundable after 45 days upon completion). Additional Monthly Fees (Both Options): $170/month for ELD, safety, and fleet support (only $40/week). $150/month for optional occupational accident insurance. Additional Benefits: We handle all factoring and paperwork so you can focus on driving. Flexible home time: 2-3 weeks out, 3-4 days at home. Requirements: No SAP (Substance Abuse Program) participation. No more than 3 moving violations in the last 3 years. No DUI offenses. At least 6 months of verifiable OTR experience. Take the Next Step in Your Career! Maximize your earnings with our competitive structure and enjoy the full support of our team. Whether you're looking for consistent runs or prefer a flexible schedule, we're here to help grow your business and ensure long-term success. Contact Us Today! 📞 ***************** 📞 *****************

NON CDL Owner-Operator - Box Truck (24ft & 26ft) | High Weekly Gross | No Forced Dispatch Join one of the top-rated carriers in the market where drivers come to stay Compensation: Weekly Gross: $6,000 to $7,500 (Solo) Top Earners: $8,000+ per week No Factoring Fees Clean DOT Inspection Bonus Sign-On Bonus Available What We Offer: No Forced Dispatch - You choose your loads OTR Across 48 States Bi-weekly home time Consistent Freight General freight - no-touch Competitive Rates & Steady Miles 24/7 Safety & ELD Support Fuel Card Program Work as an independent contractor Paid On-site Orientation Requirements: 24ft or 26ft box truck (model year 2013 or newer) Minimum 6 months of verifiable OTR experience Standard Driving License Required (NON CDL) Take control of your schedule and earnings with a company that supports your success. Apply now and let's get you on the road. Need more info? 📞*****************

P & J CARRIERS INC Find us HERE. Do you have a new MC? No problem! Use our company's connections to get consistent loads. Owner-Operators who run all week can gross $6,000 - $7,600. Take home: $3,300+ Average rate: $1.9 per mile Home time: every other week No loading or unloading 15c/gallon fuel discount OTR - 48 states Mostly Midwest and South Paid orientation in IL Requirements 24' 26' box truck Truck no older than 2013 No SAP / DUI / moving violations 6 months of verifiable OTR experience Onboarding takes only 3 days! Start today!

Job DescriptionP & J Carriers INC BOX TRUCK NON CDL Job What We Offer Weekly gross: $5,500 - $7,500+ 90% of gross goes to the driver, 10% service fee Fuel card with starting discount of $0.20/gallon Consistent OTR work across all 48 states No Forced Dispatch 24/7 support: Dispatch, ELD, safety, and roadside assistance Quick onboarding process within 2 days Requirements 24' or 26' box truck (model year 2012 or newer) Must have lift gate, pallet jack, and straps Minimum 6 months of verifiable OTR experience Familiarity with ELD systems Must operate in compliance with DOT regulations Responsibilities Operate your box truck safely and efficiently Complete OTR deliveries across the continental U.S. Secure and manage freight properly Maintain communication with dispatch Conduct vehicle inspections and keep accurate delivery logs How to Apply Call our team for more info: ************* Apply now and our team will contact you within 24 hours.

Now onboarding box truck owner-operators to move loads for our clients. Working under our MC or yours! Yes, we work with new MCs. Fuel Card Program Sign on bonus Clean DOT inspection bonus 2-day hiring process, orientation on-site Our Offer: Weekly gross $5,500 - $8,000 (solo) No factoring fees No forced dispatch OTR loads - 48 states Consistent freight, competitive rates 24/7 safety & ELD support Bi-weekly home time General freight, mostly no-touch. Requirements : 24' or 26 ' box truck Truck no older than 2013 No SAP / No more than 1 moving violation in the past 2 years Six months of verifiable OTR experience

Apply now Semi Local opening 75 miles to 400 mile radius depending on daily freight deliveries 1099 Independent Contractor position for Box truck owner operators with their own truck or trucks, possibility to self dispatch if you want Your own 26 ft Box truck required, Call ************ Semi Local, dry freight with great pay and home time for work, life balance. We value you and your family as trucking is a family decision. It involves your whole family. Excellent Home time, pay and benefits. No CDL required Current DOT Authority and MC for interstate preferred but not required Good work ethics clean background for contract customer freight The sky is the limit, get your part of it now. What are you waiting for? You will be rolling in success and have great pay, home time to $5000 Weekly Pay avg, above average owner operators can make up to 7K weekly Dry Freight Great pay and benefits Semi Local Potential to earn way more...... Driver Referral Bonus May more options available and we have all the tools for your success. What are you waiting for

Job Title: CDL Owner Operator Regional & Intermodal (Dry Van) Job Type: Contract Join our clients growing team of reliable and independent Owner Operators. If youre looking for freedom, flexibility, and a partner that respects your schedule, this opportunity is for you. With competitive revenue splits and fuel discounts, your earning potential is what you make it. Compensation & Perks: Earn 85% of load revenue a highly competitive rate Fuel card discounts: Up to 15 cents off the cash price at TA Petro Up to 12 cents off the cash price at Pilot No forced dispatch choose the loads that work for you Pick your own schedule: days and times that suit your lifestyle Regional and Intermodal Dry Van opportunities available Trailer available for weekly rental ($150/week) if you dont own one Requirements: Valid CDL with at least 2 years of experience No more than 3 moving violations within the last 3 years No OWI/DWI convictions Must own a trailer or be open to renting one weekly Why Drivers Choose Us: We put drivers first happy drivers deliver the best service. Our commitment to your independence, earning potential, and support ensures youre not just driving you're building a business. Screening Questions: Do you have a valid CDL with at least 2 years of experience? Do you currently own a trailer or are you open to a weekly trailer rental? Do you have fewer than 3 traffic violations in the past 3 years and no OWI/DWI?

Now Hiring: Box Truck Owner Operators (Bring Your Own Equipment) Join Our Growing Team and Start Earning Today! We are looking for reliable and motivated Box Truck Owner Operators to partner with us. If you own a 22'-26' box truck and are ready to maximize your income, we have the freight, support, and structure to get you moving fast! What We Offer: Gross earnings between $6,000 - $9,000 per week Take home between $2,500 - $5,000 per week (after all expenses) Consistent loads nationwide routes available 24/7 Dispatch and Operational Support Fuel Cards Expenses: 12% Dispatch Fee ELD Subscription $60/week (Tablet and Dashcam INCLUDED) Liability and Cargo Insurance $350/week (Coverage: $2M Liability / $250K Cargo) Occupational Accident Insurance $37.50/week Requirements: 22'-26' Box Truck (with liftgate preferred) Must have clean driving record and professional attitude Willingness to work hard and stay compliant Why Partner With Us? Strong, transparent communication Flexible home time No forced dispatch We care about YOUR success!

C & K Trucking is a well established nationwide Intermodal company seeking Class A Owner Operators! As one of the largest crosstown, drayage companies, we offer outstanding compensation and great benefits to our Owner Operators. Beyond these benefits, C&K Trucking provides a warm and welcoming environment where your efforts are appreciated and recognized. Come join our team and discover all that C&K Trucking has to offer for Owner Operators. Work Available: Drop & Hook Live Load/ Unload Why Lease to C & K ? Home Daily Dedicated Lanes Family Orientated Atmosphere 24/7 Dispatch National Tire Program On Site Parking Hazmat Pay Third Party Health Benefits and MORE!!!!! 1 year of Verifiable Tractor Trailer Experience No DUI within 7 years

• $3,000.00 Sign On Bonus ($3,500.00 w/ Haz Mat Endorsement) • $1,000.00 Referral Bonus • $600.00 Bonus for Clean (No Violation) Level 1 Roadside Inspection ($300.00 Bonus for Level 2 Roadside Inspections and $150.00 for level 3) • Driver Rewards Program • Weekly Settlements • Comdata Fuel Card Accounts • No Touch Freight Only • Great Pay - Steady Work - Good Equipment • Class ‘A' CDL (Haz Mat Endorsement Optional) • 2 Years of Recent Tractor Trailer Driving Experience • No More than 3 Moving Violations in the Previous 36 Months • No More than 1 Accident During Previous 36 Months • No Positive Drug or Alcohol Tests (Past or Present)

Partners Transport Express - is signing on Owner Ops/Drivers!!! We are an INTERMODAL, driver-focused company dedicated to safety and customer service. We are currently looking for Owner Operator Drivers interested in REGIONAL, LOCAL, and CROSSTOWN LANES that are HOME DAILY! Much of our regional freight goes between Western Michigan, Indianapolis and CHICAGO. We also serve IL locally and surrounding states including WI, IN, and IA regionally. DETAILS: Work available 7 DAYS A WEEK, Day and Night! Primarily 53' Containers ESTIMATED PAY: We pay 70% of the linehaul and 100% of the Fuel Surcharge to the Truck Drivers can GROSS $3000-$4000+ per week if you work five days a week. And all rates are immediately visibility upon accepting your dispatch in our App. Must be at least 23 years of age. A minimum of 2 years of verifiable Class A CDL tractor-trailer experience. Must have at least 6 months of container experience/comfortable with Chicagoland Rails Must meet Motor Carrier's IBE Qualification Standards Must have a current DOT physical Must not be prohibited in the FMCSA Drug & Alcohol Clearinghouse. Must not have more than 100 CSA points. Equipment must be model year 2000 or newer.

Trucking Opportunity with Competitive Earnings and Full Support We are offering a highly competitive compensation plan with the potential to earn up to $11,000 per week. You will receive 88% of your load and the flexibility of being your own boss while operating under our authority. Key Benefits: Up to $11,000/week in gross earnings: Maximize your income with over 4,000 miles per week. Bonuses: Safety and referral bonuses available. Flexible Home Time: Take time off when needed, while still maintaining high earnings. 24/7 Support: Access to dispatch, mechanic, and ELD support whenever you need it. Expenses: Escrow: $250/week for the first 10 weeks only. Trailer Rentals: Conestoga: $400/week Dry Van: $250/week Reefer: $450/week Insurance: Liability & Cargo: $300/week Occupational Insurance: $45/week Additional Costs: Logbook, tablet, camera: $50/week Tolls & Fuel: Weekly costs vary based on route and expenses. Requirements: This opportunity is available only to drivers who own their truck. You will operate under our authority. CDL (front and back) and medical card are required. How to Apply: If you meet the requirements and are ready to take your career to the next level, click below to apply now.

🚛 CDL-A Owner Operators - Open Deck Division . 🚛 CDL-A Owner Operators - Open Deck Division | Drive for yourself. Partner with a company that stands for something bigger. At Bennett Motor Express, we don't just offer freight - we offer freedom, family, and a foundation of faith that's helped independent contractors thrive for more than 50 years. Founded by Marcia Taylor in 1974 and still family-owned and operated, Bennett is built on the belief that when we put people first, everything else follows. We proudly serve America with integrity, patriotism, and excellence - and we treat every contractor like part of our own. We're looking for CDL-A Owner Operators who want more than just miles. If you're ready to run your business, keep more of what you earn, and partner with a company that shares your values, there's a place for you here. 💼 Divisions Now Hiring: Flatbed Step Deck Heavy Haul 💰 What You'll Get: ✅ Orientation Bonus - $1,000 ✅ Fast Pay - Every day can be payday ✅ Earn up to 74.7% of line haul revenue ✅ Industry-Leading Fuel Discounts - Save ~$5,000/year on average ✅ No Forced Dispatch - You choose your loads ✅ Tire & Parts Discounts ✅ Safety Bonus - Up to $3,000 annually ✅ Business Support - Accounting, load alerts & back-office help ✅ 24/7 Chaplain Support - Because your spirit matters too ✅ Pet & Rider Programs - Bring family along for the ride ✅ Virtual or In-Person Orientation - Your choice ✅ Medical Insurance Program Options Limited availability - Apply today! Requirements: CDL A 1 year of Verifiable OTR CDL A Experience 🌟 Why Contractors Choose Bennett: Faith-based, family-first culture You're in business for yourself, not by yourself We exist to serve people, create opportunity, make a difference, and honor God in all we do We believe in loyalty, safety, financial strength, and giving back to the communities we serve At Bennett, you don't just lease on - you level up. Let's build something meaningful together.

NON CDL Box Truck Owner Operators - National Tenant Services Inc. Apply today and start hauling within 3-4 days. You may run under NTS's authority or not. Now accepting new authorities too Weekly gross $5,500 - $7,500 (solo) No factoring fees No forced dispatch No ESCROW OTR routes only 24/7 safety & ELD support Bi-weekly home time General freight, mostly no-touch Benefits: Paid orientation Sign on bonus Clean DOT inspection bonus Requirements: 24' or 26' box truck Truck no older than 2010 NON CDL driver's license Six months of verifiable OTR experience 120-minute onsite orientation in Chicago, IL. You pick up your first load the same day! More Info: 📞 *****************

Now Hiring: Box Truck Owner Operators (Bring Your Own Equipment) Join Our Growing Team and Start Earning Today! We are looking for reliable and motivated Box Truck Owner Operators to partner with us. If you own a 22'-26' box truck and are ready to maximize your income, we have the freight, support, and structure to get you moving fast! What We Offer: Gross earnings between $6,000 - $9,000 per week Take home between $2,500 - $5,000 per week (after all expenses) Consistent loads nationwide routes available 24/7 Dispatch and Operational Support Fuel Cards Requirements: 22'-26' Box Truck (with liftgate preferred) Must have clean driving record and professional attitude Willingness to work hard and stay compliant Why Partner With Us? Strong, transparent communication Flexible home time No forced dispatch We care about YOUR success!

Attention New Rate Increases!! New Fuel Surcharge Increases! C&K Trucking needs Chicago Owner Operators for Dedicated Cross-Town / Rail to Rail Gross up to $1,000.00 a day or more - 100% Drop & Hook - Minimal B/T!! Home Daily No Cargo Insurance Fuel Discounts Terminal Parking Plan Plate Program Family Health Insurance Available Flexible scheduling 100% drop and hook loads No forced dispatch and no-touch freight Just click the link below or call us at ************ ********************************************************************************* [intelliapp.driverapponline.com]

Trucking Opportunity with Competitive Earnings and Full Support We are offering a highly competitive compensation plan with the potential to earn up to $11,000 per week. You will receive 88% of your load and the flexibility of being your own boss while operating under our authority. Key Benefits: Up to $11,000/week in gross earnings: Maximize your income with over 4,000 miles per week. Bonuses: Safety and referral bonuses available. Flexible Home Time: Take time off when needed, while still maintaining high earnings. 24/7 Support: Access to dispatch, mechanic, and ELD support whenever you need it. Expenses: Escrow: $250/week for the first 10 weeks only. Trailer Rentals: Conestoga: $400/week Dry Van: $250/week Reefer: $450/week Insurance: Liability & Cargo: $300/week Occupational Insurance: $45/week Additional Costs: Logbook, tablet, camera: $50/week Tolls & Fuel: Weekly costs vary based on route and expenses. Requirements: This opportunity is available only to drivers who own their truck. You will operate under our authority. CDL (front and back) and medical card are required. How to Apply: If you meet the requirements and are ready to take your career to the next level, click below to apply now.

P & J Carriers INC BOX TRUCK NON CDL Job What We Offer Weekly gross: $5,500 - $7,500+ 90% of gross goes to the driver, 10% service fee Fuel card with starting discount of $0.20/gallon Consistent OTR work across all 48 states No Forced Dispatch 24/7 support: Dispatch, ELD, safety, and roadside assistance Quick onboarding process within 2 days Requirements 24' or 26' box truck (model year 2012 or newer) Must have lift gate, pallet jack, and straps Minimum 6 months of verifiable OTR experience Familiarity with ELD systems Must operate in compliance with DOT regulations Responsibilities Operate your box truck safely and efficiently Complete OTR deliveries across the continental U.S. Secure and manage freight properly Maintain communication with dispatch Conduct vehicle inspections and keep accurate delivery logs How to Apply Call our team for more info: ************* Apply now and our team will contact you within 24 hours.