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Truck Driving Jobs in Chicago, IL

CDL-A Solo OTR/Regional Company Drivers Needed in Chicago, Illinois - 2500-3200 miles per week

Summitt Trucking LLC

Chicago, IL

30+ days ago
Class A CDL OTR Solo Students in Chicago, Illinois: Practical Mile Pay and Consistent Freight!SoloStudent


Chicago, IL

4 days ago
"Dedicated Team Routes" Terminal to Terminal Drop & Hook

Paramount Freight Systems

Chicago, IL

30+ days ago
Class-A CDL Truck Driving Positions - New Starting Pay: 51 to 55 CPM!! First-year Pay Range of $65,000 to $84,240!!

Dick Lavy Trucking

Chicago, IL

30+ days ago
Flatbed Truck Drivers Needed in Chicago, Illinois :: $2,625 transition pay!

Smokey Point Distributing

Chicago, IL

10 days ago
CDL-A OTR Dry Van Drivers needed in Chicago, Illinois: Weekly Home Time and NO Megafleet Micromanagement!!

Elite Carriers

Chicago, IL

30+ days ago
Seeking CDL A Owner Operators for Regional, Dedicated & OTR Routes! Hiring now in Chicago, Illinois! $1.45 per Mile!

Evennon Inc.

Chicago, IL

10 days ago
CDL-A Truck Driver - Reefer

Decker Truck Line, Inc.


20 days ago
SOLO & TEAM DRIVERS in Chicago, Illinois:: We Have the Miles and Pay You've Been Looking For! $5,000 Driver Retention Bonus!!

Sunset Logistics

Chicago, IL

11 days ago

Chicago Truck Driving Jobs Overview

Roaring down the open roads—the highway-tendons crossing the nation—truck drivers keep the pace, assert control, and skillfully transport various goods. That sense of freedom and the thrill of driving a mammoth-vehicle are major pulls for those drawn to truck-driving jobs—an expression of grace through heavy machinery. Are you big on mechanical know-how, and can you maintain focus for extended periods of time? Do you have a robust work ethic, and can you be reliable for the long haul? Then truck-driving jobs may be for you.

Although many transportation companies have dispatchers providing specific routes, independent truck drivers can plan their own journeys, enjoying the challenge of figuring out what roads allow large trucks and making time for mandated rest periods. Tasks you can expect to perform as a truck driver include loading, unloading, and recording cargo deliveries; refueling and cleaning your vehicle; and keeping your dispatcher updated and reporting any incidents.

You can expand your search for transportation jobs by checking out these similar positions:

About Working in Chicago, Illinois

If you're going to Chicago to experience "da Bears," deep-dish pizza, and windy streets, native Chicagoans say "fogetta 'bout it!" While these have made Chicago famous, you'll find many locals eating thin-crust, tavern-style pie. Plus, the city isn't on any list of the windiest cities in the U.S.—a local newspaper named it "The Windy City" after the Chicago elite's propensity toward boastfulness and self-promotion. And while the Chicago jobs list (hit jobs, that is) includes notorious mobsters from Chicago like Al Capone, John Dillinger, and Baby Face Nelson, linguists are noticing that the "Chicago accent" is disappearing.

However, there's a reason Condé Nast Traveler has named Chicago the "best big city in the U.S." Chicago is home to top universities, including Northwestern University, Wheaton College, and Valparaiso. And if you're looking for Chicago jobs, you can relocate to any one of the city's unique neighborhoods, such as North Center with its cozy Irish pubs and breweries or Uptown, the lively entertainment district. For those who want to live further out from the city, you can also find jobs in popular suburbs including Cicero, Oak Park, and Evanston.

Update Your Chicago Truck Driving Resume

Itching to hop into your semi and start delivering freight or consumer packages? Then rev-up your resume to spotlight any truck-driving experience and track record you may already have, along with relevant schooling and licensure details. You can zone in on any specializations too, such as your ability to work with hazardous materials (HAZMAT) or to maneuver pneumatic bulkers. Review Monster's truck driver resume sample for additional suggestions. Then, take a look at this example of a truck driver cover letter to ensure a smooth ride when you have to write one.

How Much Do Truck Driving Jobs Pay in Chicago, Illinois?

Got money on your mind? You should! Make sure you’re getting paid what you’re worth. Our Salary Tools can help you understand what you can expect to make in truck driving jobs in Chicago, Illinois, as well as the skills that can boost your value and what the next steps in your career might be. Right now, the median HAZMAT truck driver pay in Chicago is $59,302 per year, which is 8% higher than the national average.

Find Your Next Chicago Truck Driving Job. Monster Can Help Get You Started

Are you prepared for a career in truck driving? If so, set up your profile on Monster for free and begin clicking on those truck driving jobs. When you sign up with us, you’ll receive custom job alerts and expert advice on how to negotiate your salary in Chicago, how to nail your job interview, and more.