Truck Driving Jobs in Chicago, IL

Trucking Jobs in Chicago

We offer a range of truck driving jobs to apply to as a commercial driver.
Enter your ZIP code below to see which CDL A driver jobs are available in your area.

Dry Van Flatbed Hazmat & Doubles Lease & Owner Operator

Dry Van

REGIONAL DRY VAN SOLO

70 CPM All Miles

$1,260 Gross Weekly Avg.

Home
weekly

$2,500 sign-on bonus

Health, dental, vision, 401k, paid time off

Orientation, clean inspection pay, and referral bonus

Detailed pay scale and benefits

APPLY NOW

OTR DRY VAN SOLO

65 CPM All miles

$1,625 Gross Weekly Avg.

Home EVERY
2 – 4 WEEKS

$2,500 sign-on bonus

10 CPM Safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW

OTR DRY VAN TEAM

77 CPM All Miles

$3,850 Gross Weekly Avg.

Home every
2 – 4 weeks

$10,000 sign-on bonus

5 CPM safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed payscale and benefits

APPLY NOW

Flatbed

OTR FLATBED SOLO

65 CPM All Miles

$1,725 Gross Weekly Avg.

Home every
2 – 4 weeks

$5,000 sign-on bonus

5 CPM bonus on 11k+ miles monthly

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW

Hazmat & Doubles

OTR HAZMAT SOLO

65 CPM + 4 CPM All Miles

$1,725 Gross Weekly Avg.

Home every
2 – 4 weeks

$2,500 sign-on bonus

10 CPM safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW

OTR HAZMAT TEAM

77 CPM + 4 CPM All Miles

$4,050 Gross Weekly Avg.

Home every
2 – 4 weeks

$10,000 sign-on bonus

5 CPM safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW

OTR DOUBLES TEAM

77 CPM + 4 CPM All Miles

$4,050 Gross Weekly Avg.

Home EVERY
2 – 4 WEEKS

$10,000 sign-on bonus

5 CPM safety/ productivity bonus

Health, dental, vision, 401k, paid time off

Detailed pay scale and benefits

APPLY NOW

Lease & Owner Operator

OWNER OPERATOR OTR

75% of load

$4,650 Gross Weekly Avg.

Home every 2 weeks

$100 Clean inspection bonus

Referral bonus of $2,000

All paperwork done by HMD

Detailed pay scale and benefits

APPLY NOW

OWNER OPERATOR REGIONAL

75% of load

$3,700 Gross Weekly Avg.

Home weekly

$100 Clean inspection bonus

Referral bonus of $2,000

All paperwork done by HMD

Detailed pay scale and benefits

APPLY NOW

DRY VAN LEASE PURCHASE

579 Peterbilt

No credit
check

Walk away
option

Multiple down payment options including 0 (zero) down

Fuel discount program available

Detailed pay scale and benefits

APPLY NOW

FLATBED LEASE PURCHASE

567 Peterbilt

No credit
check

Walk away
option

$0 buyout

Multiple down payment options including 0 (zero) down

Fully equipped trailer in lease $200/wk

Detailed pay scale and benefits

APPLY NOW

Trucks You'll Drive

Our fleet keeps growing. Today, HMD Trucking operates over 500 modern trucks. Drivers working with us enjoy top-class vehicles while taking on CDL driver jobs in Chicago and beyond — handling all types of freight and ensuring safe, on-time delivery.

At HMD Trucking, Every Semi Truck Is Outfitted with Modern Features That Put Driver Comfort, Safety, and Performance First

Spacious, high-roof cabin
Inverter
Powerful diesel APU
Minifridge
Automatic or manual
Removable rider seat
Comfortable combo sleeper

We make sure every truck and tractor trailer stays in top condition. Our in-house maintenance shop is fully stocked and staffed by skilled mechanics, making sure every rig stays in top shape, mile after mile. That’s the foundation of safe and smooth commercial driving.

Apply now

579

567

What Makes Truck Driving Job at HMD Enjoyable

We’re a top-rated transportation company serving routes across the United States. Our openings include truck driver jobs in Chicago, IL — with opportunities for both experienced and new drivers.

Key benefits for drivers

Drive newer trucks paired with high-quality trailers as a commercial driver

Enjoy full medical benefits: health, dental, vision & 401K

Count on 24/7 support from a responsive and reliable team

A few real stats coming directly from our drivers

79%

are highly satisfied with how dispatch keeps things running

81%

chose us for clear, honest communication with recruiters

87%

appreciate the top-notch maintenance on their trucks

See How Much You Can Earn at Hmd

Ready to join? Apply now for truck driver jobs in Chicago, Illinois — it only takes a minute.

OTR Dry Van Solo

May 2025

Ennio K.

Miles

13,290

Base CPM, $

0.60

Pay, $

7,974

Bonus pay CPM, $

0.10

Bonus pay, $

1,329

Total, $

9,303

Roman K.

Miles

12,427

Base CPM, $

0.60

Pay, $

7,456

Bonus pay CPM, $

0.08

Bonus pay, $

994

Total, $

8,450

Chris B.

Miles

14,530

Base CPM, $

0.60

Pay, $

8,718

Bonus CPM, $

0.08

Pay, $

1,162

Total, $

9,880

OTR Dry Van Teams

May 2025

Steve B. and Michael F.

Miles

23,160

Base CPM, $

0.77

Pay, $

17,833

Bonus pay CPM, $

0.05

Bonus pay, $

1,158

Total, $

18,991

Juan M. and Peter B.

Miles

22,144

Base CPM, $

0.77

Pay, $

16,973

Bonus pay CPM, $

0.05

Bonus pay, $

1,107

Total, $

18,080

OTR Flatbed Solo

May 2025

Michael W.

Miles

15,128

Base CPM, $

0.65

Pay, $

9,833

Bonus pay CPM, $

0.05

Bonus pay, $

756

Load pay, $

630

Total, $

11,219

Muchael R.

Miles

13,827

Base CPM, $

0.65

Pay, $

8,988

Bonus pay CPM, $

0.05

Bonus pay, $

691

Load pay, $

510

Total, $

10,189

OTR Hazmat Solo

May 2025

Adam F.

Miles Dry Van

4,600

Miles Hazmat

7,680

Dry Van CPM, $

0.60

Dry Van Pay, $

2,760

Hazmat CPM, $

0.64

Hazmat pay, $

4,915

Bonus CPM, $

0.10

Bonus pay, $

1,228

Total, $

8,903

Gregory J.

Miles Dry Van

5,100

Miles Hazmat

8,700

Dry Van CPM, $

0.60

Dry Van Pay, $

3,060

Hazmat CPM, $

0.64

Hazmat pay, $

5,568

Bonus CPM, $

0.08

Bonus pay, $

1,104

Total, $

9,732

OTR Hazmat Teams

May 2025

Bobby B. Katherine M.

Miles Dry Van

5,120

Miles Hazmat

18,310

Dry Van CPM, $

0.77

Dry Van Pay, $

3,942

Hazmat CPM, $

0.81

Hazmat pay, $

14,831

Bonus CPM, $

0.05

Bonus pay, $

1,172

Total, $

19,945

Joe M. Kyle M.

Miles Dry Van

5,505

Miles Hazmat

19,500

Dry Van CPM, $

0.77

Dry Van Pay, $

4,239

Hazmat CPM, $

0.81

Hazmat pay, $

15,795

Bonus CPM, $

0.05

Bonus pay, $

1,250

Total, $

21,284

OTR Doubles Teams

May 2025

Davis L. Nathan A.

Miles Dry Van

5,395

Miles Doubles

19,335

Dry Van CPM, $

0.77

Dry Van Pay, $

4,154

Doubles CPM, $

0.81

Doubles pay, $

15,661

Bonus CPM, $

0.05

Bonus pay, $

1,237

Total, $

21,052

Edier M. Janet M.

Miles Dry Van

5,220

Miles Doubles

18,900

Dry Van CPM, $

0.77

Dry Van Pay, $

4,019

Doubles CPM, $

0.81

Doubles pay, $

15,390

Bonus CPM, $

0.05

Bonus pay, $

1,206

Total, $

20,534

Regional Dry Van Solo

May 2025

Harold A.

Miles

10,490

Base CPM, $

0.65

Pay, $

7,868

Total, $

7,868

Austin P.

September 2023

Miles

9,080

Base CPM, $

0.65

Pay, $

5,902

Total, $

5,902

Ryan N.

September 2023

Miles

9,790

Base CPM, $

0.65

Pay, $

6,364

Total, $

6,364

APPLY NOW

Explore your earning potential as a company driver in our team. Pick one of the available vacancies from the list below and see real paycheck examples from CDL Class A drivers — so you know exactly what to expect on the road with us.

About HMD Trucking

HMD Trucking began as a small family business in 1998 and has grown into a respected name in freight transportation across the United States.

Today, we operate a fleet of over 500 modern trucks, delivering flexible, dependable hauling solutions to clients nationwide — and expanding our reach every year. We provide CDL A jobs in Chicago, IL and beyond — offering professional drivers stable work, modern equipment, and room to advance.

Truck Driving Jobs in Chicago, IL

Trucking Jobs in Chicago

Trucks You'll Drive

What Makes Truck Driving Job at HMD Enjoyable

See How Much You Can Earn at Hmd

About HMD Trucking

Trucking Jobs In