Now hiring in Chicago

Trucking Jobs in Chicago, IL: CDL-A Driver Jobs

Explore Local, Regional and Monday–Friday OTR CDL-A driver opportunities serving Chicago and Northeast Illinois. Compare schedules, home time, freight and requirements, then apply directly. Browse trucking jobs and CDL-A truck driving jobs from participating motor carriers.

Choose your schedule

Current Chicago CDL-A openings

Openings and assignments can change. Select a position to review its current details and submit your information.

LOCAL · HOME DAILY

Local CDL-A Driver

Local routes with home time every night

Primarily 53-foot, drop-and-hook, no-touch freight

View job and apply

REGIONAL · ONE NIGHT OUT

Regional CDL-A Driver

Typically one night out followed by one to three nights home

Primarily 53-foot, drop-and-hook, no-touch freight

View job and apply

OTR · FIVE-DAY ROTATION

Monday-Friday OTR CDL-A Driver

Five days over the road with expected weekend home time

Primarily 53-foot, drop-and-hook, no-touch freight

View job and apply

The local market

Driving opportunities around Chicago

Chicago is one of North America's largest freight and intermodal hubs, connected by I-55, I-57, I-80, I-90 and I-94. These openings are for qualified drivers who can report reliably throughout the Chicagoland market.

Common reporting area: Chicago, Joliet, Aurora, Elgin, Schaumburg, Gary and surrounding Chicagoland communities.

Common minimum requirements

  • Valid Class A CDL and DOT medical card
  • Age 21 or older
  • At least three months of experience or qualifying CDL school
  • Ability to pass required background and drug screening
  • Safe, reliable operation of a 53-foot tractor-trailer

The participating motor carrier determines final eligibility. Requirements may vary by opening.

What drivers can expect

Clear schedules

Compare local, regional and OTR rotations before you apply.

Qualification guidance

A recruiter helps explain documentation, screening and onboarding steps.

Direct application

Apply for a specific market and schedule without searching through unrelated positions.

Frequently asked questions

What trucking jobs and CDL-A truck driving jobs are available in Chicago, IL?

Current Chicago openings include Local and Regional and Monday-Friday OTR. Availability can change as participating motor carriers fill driver seats.

Which communities are included in the Chicago hiring area?

The common reporting area includes Chicago, Joliet, Aurora, Elgin, Schaumburg, Gary and surrounding Chicagoland communities. Final reporting locations are confirmed by the participating motor carrier.

What license and experience are required for Chicago CDL jobs?

Applicants must hold a valid Class A CDL. Many openings seek at least three months of tractor-trailer experience or qualifying CDL-school completion, subject to the carrier's final requirements.

What freight do Chicago drivers haul?

Most listed opportunities involve 53-foot trailers with primarily drop-and-hook, no-touch freight. Confirm the exact assignment with recruiting.

Does submitting an application guarantee employment?

No. CDL Driver Hire and Roger That Recruiting coordinate recruiting. The participating motor carrier makes all final qualification and hiring decisions.

Need help choosing an opening?

Speak with a real recruiter at Roger That Recruiting.

Call 813-738-7858