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Driver Trainee Jobs in Chicago, IL (NOW HIRING)

WeDriveU

Paratransit Driver - CDL

Lansing, IL · On-site

$24.16/hr

All interested applicants for a Transit Driver position begin with us as a Driver Trainee. The best-trained drivers in the business work for us because we devote a significant amount of resources ...

WeDriveU

Transit CDL Driver

Niles, IL · On-site

$25/hr

All interested applicants for a Transit Driver position begin with us as a Driver Trainee. The best-trained drivers in the business work for us because we devote a significant amount of resources ...

WeDriveU

Paratransit Driver - CDL

Lansing, IL

$24.16/hr

All interested applicants for a Transit Driver position begin with us as a Driver Trainee. The best-trained drivers in the business work for us because we devote a significant amount of resources ...

WeDriveU

Transit CDL Driver

Niles, IL

$25/hr

All interested applicants for a Transit Driver position begin with us as a Driver Trainee. The best-trained drivers in the business work for us because we devote a significant amount of resources ...

INDIANA BEVERAGE INC

SALES TRAINEE

Valparaiso, IN · On-site

$45K/yr

SALES TRAINEE - Lake and Porter County Starting Annual Salary: $45,000 Join an Award-Winning Team ... Must be 21+ with a valid driver's license and clean driving record * Ability to pass background ...

WeDriveU

Paratransit Driver Non CDL

Chicago, IL

$24/hr

Note: Interested applicants for a Transit Driver position may begin with us as a Driver Trainee. The best trained drivers in the business work for us because we devote a significant amount of ...

WeDriveU

Paratransit Driver Non CDL

Chicago, IL · On-site

$24/hr

Note: Interested applicants for a Transit Driver position may begin with us as a Driver Trainee. The best trained drivers in the business work for us because we devote a significant amount of ...

WeDriveU

Paratransit Driver Non CDL

Chicago, IL · On-site

$16.50 - $19.75/hr

Note: Interested applicants for a Transit Driver position may begin with us as a Driver Trainee. The best trained drivers in the business work for us because we devote a significant amount of ...

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Bolingbrook, IL · On-site

$17.84 - $26.76/hr

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Bolingbrook, IL · On-site

$17.84 - $26.76/hr

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Bolingbrook, IL · On-site

$17.84 - $26.76/hr

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Bolingbrook, IL · On-site

$17.84 - $26.76/hr

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Red Bull

Sales Trainee

Arlington Heights, IL · On-site

This is a training role that is made to prepare the Sales Trainee for the Account Sales Manager ... Valid US Driver's License and obtainment of DOT Medical card * Obtainment of DOT Medical card

Compass Transportation

Safety Trainer

Chicago, IL

$50K - $60K/yr

The recruiter will be responsible to identify and recruit potential drivers and trainees to our company. The Safety trainer will make sure the company maintains compliance with all Federal and State ...

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Showing results 21-40

All JobsDriver JobsDriver Trainee JobsDriver Trainee Jobs in Chicago, IL

Driver Trainee information

See Chicago, IL salary details

$25.8K

$51.5K

$68.5K

How much do driver trainee jobs pay per year?

As of Aug 22, 2026, the average yearly pay for driver trainee in Chicago, IL is $51,459.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,200.00 and $59,700.00 per year, depending on experience, location, and employer.

What is a driver trainee?

A driver trainee works with an employer to gain the knowledge and experience necessary to haul freight and operate tractor trailers. It usually involves the training you need to get a commercial driver's license (CDL). The process varies with the company, but it typically includes a combination of classroom time, safety coursework, and on-the-job route driving. Depending on the materials you carry, your duties may also involve earning additional license endorsements, such as hazardous material (HAZMAT). Your responsibilities may also be to load and unload trucks. You also have to record your work hours as per state and federal regulations.

What are the key skills and qualifications needed to thrive as a driver trainee?

To thrive as a Driver Trainee, you typically need a high school diploma or GED, a valid driver’s license, and a clean driving record. Familiarity with GPS navigation systems, vehicle inspection procedures, and, eventually, a Commercial Driver’s License (CDL) are often required. Strong attention to safety, good communication, and a willingness to learn help trainees adapt quickly and work well with supervisors and customers. These skills and qualifications ensure safe driving practices, regulatory compliance, and readiness for advancement to full professional driving roles.

What types of training and support can I expect as a driver trainee?

As a Driver Trainee, you will typically participate in a structured training program that combines classroom instruction with on-the-road experience under the supervision of experienced drivers or instructors. You'll learn about vehicle safety, regulatory compliance, route navigation, and proper loading/unloading procedures. Most employers provide mentorship and regular feedback during training, ensuring you build confidence and develop safe driving habits before transitioning to independent routes. This supportive environment helps you gradually assume more responsibility while preparing for any required licensing exams.

What is the difference between Driver Trainee vs Driver?

AspectDriver TraineeDriver
Required CredentialsDriver's license, possibly a commercial licenseValid driver's license, commercial license if applicable
Work EnvironmentTraining sites, company vehicles, on-the-job trainingRegular routes, delivery or transportation settings
Employer & Industry UsageEntry-level position in transportation, logistics, or delivery companiesFull-time professional role in similar industries

Driver Trainee is an entry-level position where individuals learn driving skills and gain necessary certifications. Once training is complete, they typically advance to a Driver role, which involves operating vehicles regularly in transportation or delivery services. The main difference lies in experience level and job responsibilities, with Driver Trainee focusing on learning and development.

More about Driver Trainee jobs

What are the most commonly searched types of Driver jobs in Chicago, IL?

The most popular types of Driver jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Driver Trainee jobs?

Cities near Chicago, IL with the most Driver Trainee job openings:

Driver Trainee jobs near you
Infographic showing various Driver Trainee job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 27% Part Time, and 2% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $51,459 per year, or $24.7 per hour.

Assistant Branch Manager Trainee

Thillens Inc

Chicago, IL

$22 - $26/hr

Full-time

Medical, PTO

Re-posted 16 days ago

Job description

We are one of the largest independently owned armored transportation and cash-logistics companies in the Midwest, operating multiple branches across Illinois and Wisconsin — and we’re growing fast.

The Assistant Branch Manager Trainee role is a paid leadership-track position designed to develop future Assistant Branch Managers and Branch Managers in a secure, regulated environment. An idea applicant. will have a valid FOID card. If this is you, please look at our other requirements and apply today.

You will begin with hands-on operational experience and progress into structured leadership training.

Assistant Branch Manager Trainee Training

Training is based in the Chicago area (company headquarters) and provides full exposure to route operations and branch leadership.

Phase 1 – Route & Operations (˜60 days):
• Route operations, safety, procedures, and customer service

Phase 2 – Office & Leadership (90–120 days):
• Training with a Senior Branch Manager
• Scheduling, employee supervision, compliance, and performance management

After training, you will be placed in a home branch based on business needs and performance.

Assistant Branch Manager Trainee Pay & Benefits

• Assistant Manager Trainee: $22.00 – $26.00 per hour + bonus
• Assistant Branch Manager: $50,000 – $60,000 + bonus
• Branch Manager: $60,000 – $85,000 + bonus

(Pay is based on experience and performance; bonuses are discretionary.)

Benefits include:
• Medical PPO & HSA plans
• AFLAC supplemental benefits
• Paid vacation
• Employee referral bonuses
• Annual firearm training
• $1,000 sign-on bonus (paid after one year of service)
• Strong, team-oriented culture
• Promotion from within strongly encouraged

Assistant Branch Manager Trainee Responsibilities & Qualifications

• Support armored route operations
• Learn branch scheduling, staffing, and compliance
• Assist with training and mentoring employees
• Support safety, security, and performance standards
• Reliable, professional, and detail-oriented
• Comfortable working in a regulated, fast-paced environment

Assistant Branch Manager Trainee Requirements

• At least 21 years of age
• Valid driver’s license and clean driving record
• Ability to pass background checks and DOT requirements
• Ability to lift 50 lbs or more

Highschool/GED completed

Licensing Requirements:
• Illinois: Ability to obtain and maintain a valid FOID card
• Wisconsin: Ability to obtain 108 Security Permit (DSPS)

Security or firearm experience is helpful, but not required — training is provided.

Why Join Us

• Clear leadership career path
• Structured training and mentorship
• Stable, growing company
• Opportunity to manage and lead a branch

Ready to Apply? If you’re looking for a long-term leadership opportunity with a growing regional company, apply today.

Apply