448 Results for

OTR Driver Jobs in Chicago, IL

Jobs

New!

Joliet, IL3 days ago

Become part of a team that invests in your future, pays you what you’re worth, and gives you the chance to master every corner of the tanker industry. Travel nationwide and support multiple terminals (including occasional air travel).

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Chicago Heights, IL4 days ago

As a family-owned, family-focused, family-driven company, we are committed to offering CDL-A regional truck driving careers with weekend home time, stable freight and excellent earning power while making safety a top priority. Step back from making a mega-carrier mistake and take a closer look at the difference it makes to work with the driver and family-focused team as a CDL-A regional truck driver at McLeod Express!

Chicago, IL10 days ago

$4,450–$5,600 Per Week

At Anderson Trucking Service (ATS), our OTR Dry Van Lease Operator program gives you access to quality freight, newer equipment, and full backing from a trusted carrier. Cloud, Minnesota, ATS has built a reputation for supporting drivers, providing reliable freight, and maintaining newer equipment.

Chicago, IL11 days ago

Minimum of 6 months of verifiable OTR tractor-trailer experience in the last 12 months or 12+ Months Experience in Last 2 Years. Must be 23 years of age or older (21 years if prior military).

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Chicago, IL4 days ago

$85,000–$90,000 Per Year

2,600 - 3,000 miles per week with high refrigerated freight volume. Navajo Express is Now Hiring CDL-A OTR Refrigerated Company Drivers.

New!

Dolton, IL4 days ago

$15.63–$41.54 Per Hour

Please be advised that Artificial Intelligence (AI) tools may be used to support certain stages of the recruitment process but are not used as a replacement for human decision making. Clean Harbors is looking for a OTR Class A Dry Van Driver to join their safety conscious team in Omaha, NE!

Homer Glen, IL7 days ago

$250,000–$400,000 Per Year

See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions. Industry's Leading Contracts with Top Earnings Potential: (Drivers are averaging $250,000-$400,000 Gross annually).

New!

Worth, ILToday

Bonus: Monthly safety bonus ($175/month); DOT inspection bonus ($50-$100 based on clean inspection. Employment with Road Warrior Staffing is contingent upon successfully passing a pre-employment background check and drug screen.

New!

Chicago, IL3 days ago

$56,888–$109,383.56 Per Year

OUR MODERN TRUCKS ARE METICULOUSLY MAINTAINED FOR YOUR SAFETYEvery tractor has a lane departure & forward collision warning system, hard brake monitoring, and a satellite communication device installed. Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate.

New!

Chicago, IL3 days ago

$56,888–$109,383.56 Per Year

New!

Chicago, IL3 days ago

$56,888–$109,383.56 Per Year

Calumet City, IL14 days ago

$25–$28 Per Hour
Full-time
Employee

We are hiring experienced OTR Truck Driver CDL-A for port and long-haul operations. Candidates with port experience and a valid TWIC Card will be highly preferred.

New!

Hammond, IN1 day ago

$85–$110 Per Year

Owner Operator Job Offers Salary: $200,000-$325,000+ Apply now to receive your job offers! Higher pay, increased benefits or more home-time: You choose.

New!

Melrose Park, IL4 days ago

See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions. Services include refrigerated LTL, dry LTL, dedicated truck loads, air freight, intermodal, warehousing and cold storage.

New!

Joliet, IL3 days ago

New!

Buffalo Grove, IL4 days ago

$45–$60 Per Hour

Today, May Trucking Company operates a fleet of more than 1,000 tractors, providing transportation services for refrigerated and dry products throughout the United States. May Trucking Company began in Payette, ID, in 1945, hauling sacks of cement to construction sites.

Arlington Heights, IL8 days ago

$51,000–$103,000 Per Year

Orientation every Tuesday at our state-of-the-art HQ in North Liberty, IAGet your assigned truck by Friday. Latest Kenworth, Freightliner, & International tractorsOur trucks run 68 MPH.

New!

Wauconda, IL5 days ago

See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions. Primarily Midwest and Southern Region, average 2500 miles per week.

New!

South Holland, IL1 day ago

$500–$600 Per Week

With preferred traffic lanes, strong percentage pay, and programs designed to support contractors-not nickel-and-dime them-Blair gives drivers the freedom to run their business with confidence. From weekend home time to transparent settlements and low-cost support, Blair focuses on keeping you moving, earning, and in control.

Chicago, IL10 days ago

$65,000–$97,000 Per Year

Earn $65,000-$97,000 per year per driver - average is $70,000 per year per driverEarn an additional 5 CPM paid for all miles north of MD and east of I-81. Latest Kenworth, Freightliner, & International tractorsWe buy new and keep it while under warrantee to have better uptime for you to keep rolling.

New!

Oak Lawn, IL4 days ago

$60,000–$99,000 Per Year

Earn $60,000-$99,000 per year - average is $72,000 per yearEarn an additional 5 CPM paid for all miles driven north of MD and east of I-81. Latest Kenworth, Freightliner, & International tractorsWe buy new and keep it while under warrantee to have better uptime for you to keep rolling.

New!

Chicago, IL2 days ago

$55–$57 Per Week

Founded in 1974, Indian River Transport provides reliable, competitive interstate, intrastate, and international transportation of bulk food-grade commodities. As a leader in bulk liquid food-grade tank carriers, Indian River Transport sets the tone for the rest of our industry.

New!

Gary, IN1 day ago

$0.55–$0.61 Per Year

All pay and bonus amounts may vary by job type, location, experience level, and performance and are subject to change based on company discretion. Typically 10-14 days out with bi-weekly home time, running strong, steady miles across Dart's 30-state network.

New!

Hammond, IN1 day ago

Enjoy 99% no-touch freight, competitive accessorial pay, strong Hazmat pay, and bonuses-including a $2,000 maintenance bonus* for new contractors, the Dart Diamond Rewards annual bonus and a $3,000 referral bonus.*. Pick steady miles and stability, ride high as your own boss, or step into truck ownership with programs designed to reduce risk and increase earning power.

Oakbrook, KY21 days ago

$1,800–$2,000

Regional Class A CDL Drivers - $1,800 - $2,000 weekly pay. If you're 22 or older, have a Class A CDL, and have at least one year of tractor-trailer experience, we want to hear from you!

New!

Hammond, IN1 day ago

From pet-friendly trucks to climate-controlled kennels and dog runs, we've built a place where both you and your co-pilot are taken care of every mile. Drivers average $85,000 per year, or about $1,635 per week, running consistent OTR miles*.

New!

Chicago, IL1 day ago

$1,400–$1,600

We know drivers are the backbone of our success, and we work hard to create a safe, supportive environment where your experience is valued and your performance is rewarded. Strong earnings averaging $1,400-$1,600, with 60-61CPM base pay, plus safety and performance incentives built in.*.

New!

Chicago, IL4 days ago

I agree that calls may be made using an automatic telephone dialing system and/or an artificial or prerecorded voice and that messages and emails may be sent using automatic messaging systems. I additionally agree that Western Express, Inc.'s service provider receives in real-time and logs your text messages and emails with Western Express, Inc.

New!

Chicago, IL4 days ago

$0.59–$0.63 Per Year

We offer truckload, dedicated, and intermodal services throughout the eastern United States, with terminals located in Tennessee, Missouri, North Carolina, and Kentucky. Ozark Motor Lines, Inc. partners with drivers across the Mid-South to keep vital supply chains moving.

New!

Dolton, IL4 days ago

$15.63–$41.54 Per Hour

New!

Dolton, IL4 days ago

$15.63–$41.54 Per Hour

Oak Park, IL10 days ago

$70,000–$80,000 Per Year

We’re hiring Local, Regional, and OTR CDL-A drivers with routes designed to fit your lifestyle. Whether you’re looking for daily home time or steady long-haul miles, Dart has an option that works for you.

New!

Chicago, IL1 day ago

$1.05–$3.50 Per Hour

No need to source freight or manage billing, compliance, or collections-Roadrunner handles it, so you can focus on driving and earning. All pay and bonus amounts may vary by job type, location, experience level, and performance and are subject to change based on company discretion.

Chicago, IL10 days ago

$56,949.36–$102,993.80 Per Year

That’s right recent CDL-A graduates—qualified applicants with a valid CDL-A license may have the opportunity to receive training and start their driving career with us during this special period and special offer, only valid through May 31, 2026. Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate.

New!

Chicago, ILToday

$1.05–$3.50 Per Hour

Teams running with Roadrunner average $8,000 or more per week paid to the truck* - a level of revenue that's simply out of reach for solo drivers. Roadrunner recommends teams stay out 2+ weeks to maximize earning weeks, but the schedule is yours to run.

Calumet City, IL10 days ago

$56,888–$109,383.56 Per Year

New!

Mundelein, IL4 days ago

$1,400–$1,550 Per Week

With more than 35 years of expertise, our owners and executives know how to support their drivers, keep the fleet operating smoothly, and foster a culture of hard work so drivers can succeed. K&B Transportation is now offering a new, competitive Home Weekend option for drivers in select Midwest and Central U.S. locations.

New!

Gary, IN1 day ago

$0.55–$0.66 Per Hour

Run 2,200-2,500+ miles per week on steady OTR freight, staying out about two weeks at a time with planned home time built into a reliable work-rest rhythm. Average 2,200-2,500+ miles per week on consistent OTR lanes, typically running one to two weeks out with structured time off you can plan around.

New!

Naperville, IL1 day ago

$90,000–$95,000 Per Year

With multiple driving opportunities, late-model equipment, and a freight network designed to keep you moving-not waiting-you can choose the path that fits your goals and grow your income your way. Run 2,500-3,000 miles per week across the Midwest, Mid-Atlantic, and Southeast-no NYC and mostly drop + hook to keep your week moving smoothly.

Chicago, IL12 days ago

$1.30–$1.40 Per Hour

Guaranteed raise at 6 months, 1 year, and 18 months OR Guaranteed 1st anniversary raise PLUS .05 CPM when you exceed 20,000 monthly miles (depending on location). Minimum of 6 months of verifiable OTR tractor-trailer experience in the last 12 months or 12+ Months Experience in Last 2 Years.

Lombard, IL13 days ago

With pathways for career advancement, from the roads to the offices, Millis Transfer is a family where you can climb the ladder to success within our supportive community. This isn’t merely a workplace; it’s a community where your efforts are acknowledged, your role is crucial, and your presence makes a difference.

New!

Franklin Park, IL4 days ago

Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate. See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions.

New!

Griffith, IN4 days ago

Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate. That's right Recent CDL-A graduates—qualified applicants with a valid CDL-A license may have the opportunity to receive training and start their driving career with us during this special period and special offer, only valid through May 31, 2026.

New!

Chicago, IL1 day ago

$60–$65 Per Hour

With multiple driving opportunities, late-model equipment, and a freight network designed to keep you moving-not waiting-you can choose the path that fits your goals and grow your income your way. Independent operators get higher earning potential and business flexibility without the heavy commitment-or financial risk-of full ownership.

New!

Chicago, IL1 day ago

About Us: Founded in 1996 and based in Wind Gap, Pennsylvania, Brothers Auto Transport is a trusted vehicle hauler in the Eastern U.S. In 2025, Brothers became the newest brand within Proficient Auto Logistics, joining six other elite operators in one national vehicle transport network. Visually clean, no oil leaks, no major structural damage, no visual defects and capable of representing company quality service commitments.

New!

Chicago Heights, IL3 days ago

$90,000–$100,000 Per Year

Werner's Career Track Program allows drivers to focus on the enhancement of their skills by getting valuable, hands-on experience with one of our highly skilled Leader Drivers. Whether you’re a seasoned veteran with a knack for hauling refrigerated freight or just starting your career, we have truck-driving jobs available to fit all levels of experience.

New!

Hammond, IN1 day ago

$600–$700

Lease Purchase drivers average $6,000 gross per week, earning 72% of linehaul plus fuel surcharge, turning steady freight into serious weekly income. Whether you're running as a company driver or stepping into a Lease Purchase role, Suit offers respectful dispatch, predictable freight, and real support.

New!

Chicago, IL1 day ago

$60–$69 Per Week

With decades of experience and a reputation built on safety and integrity, we provide the tools, equipment, and culture to help you succeed on and off the road. All pay and bonus amounts may vary by job type, location, experience level, and performance and are subject to change based on company discretion.

New!

Merrillville, IN1 day ago

$65–$72 Per Hour

New!

Chicago, IL1 day ago

$60–$69 Per Week

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OTR Driver Jobs in Chicago, IL

CDL-A Tanker Driver - OTR Kenan Advantage Group

CDL A Regional OTR Truck Driver McLeod Express

OTR CDL-A Truck Driver Anderson Trucking Service

OTR Team CDL-A Company Truck Drivers - Multiple Locations - $15,000 Sign-On Bonus per team (limited time) Transco Lines, Inc.

OTR CDL-A Truck Driver Navajo Express

OTR Class A Dry Van Driver Clean Harbors

CDL OTR Moving Driver American Van Lines

CDL A-OTR Truck Driver Illinois Road Warrior

Flatbed CDL-A OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits System Transport

Class A CDL Flatbed OTR Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits System Transport

CDL-A OTR Flatbed Driver: Earn $1,094.00 – $2,103.53 per week. Full Benefits System Transport

OTR Truck Driver Utopia Fulfillment

OTR CDL-A Truck Driving Jobs (Earn $85k - $110k+ a Yr!) Apply Now! Hiring Drivers Now

OTR CDL A Driver Home Weekends GT Expedited

CDL A Truck Driver - Hiring Statewide Kenan Advantage Group

CDL-A Truck Driver May Trucking Company

CDL-A Truck Driver Heartland Express

OTR Lease Operator ACA Truck Leasing

CDL A Truck Driver - 1099 Blair Logistics Inc

Experienced CDL-A Team Truck Drivers - Earn $65,000-$97,000/Year Heartland Express

CDL-A Truck Driver - Earn $60,000-$99,000/Year Heartland Express

CDL-A Tanker Truck Driver Indian River Transport

CDL A Truck Driver - $2,000 Sign-On Dart Transit

Regional Truck Driver: 99% no-touch, 1099 options Dart Transit

Regional CDL A Drivers Premier Transportation

CDL A Truck Driver J.S. Helwig & Son

CDL A Truck Driver - up to $1,600+ / wk Kivi Bros Trucking

CDL-A Truck Driver - No Experience Needed! Western Express, Inc.

CDL-A Truck Driver Ozark Motor Lines, Inc.

Truck Driver Clean Harbors

CDL A Truck Driver Clean Harbors

CDL-A Truck Driver - 100% No-Touch Freight Dart

CDL A Owner Operator Drivers Roadrunner

CDL-A Truck Driver - Recent Grads Welcome System Transport

CDL A Owner Operator Team Drivers Roadrunner

CDL-A Flatbed Truck Driver System Transport

CDL-A Truck Driver - Home Weekly K&B Transportation

CDL A Truck Driver - up to $92k / yr J&R Schugel

Reefer Truck Driver - up to $130k / yr EOS Trucking

Hiring Class A CDL Team Truck Drivers - Multiple Locations - $15,000 Sign-On Bonus per team Transco Lines, Inc.

CDL-A Truck Driver Millis Transfer

Flatbed CDL Driver, Regional Route System Transport

Recent Flatbed CDL Driver System Transport

CDL A Truck Driver - 1099 - Up to $130k / yr EOS Trucking

CDL-A Owner Operator Auto Haulers Needed: Earn $250,000–$350,000+ per year, Regional and OTR Routes Proficient Auto Transport

CDL-A Truck Driver Werner Enterprises

CDL A Truck Driver - 1099 - $5,500 / wk Suit Transportation

Regional CDL-A Truck Driver - up to $2,000 / wk E.W. Wylie

Specialized CDL A Truck Driver - $3500 Onboarding Pay E.W. Wylie

CDL A Truck Driver - up to $120,000 / yr E.W. Wylie

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