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CDL A Jobs in Chicago, IL

Explore top CDL A jobs in Chicago, IL and find the perfect driving opportunity that fits your lifestyle and supports your family.

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

65 CPM All Miles
$1,200 Gross Weekly Avg.
Home
weekly

No touch freight

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

Orientation, clean inspection pay, and referral bonus

Detailed pay scale and benefits

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OTR DRY VAN SOLO

60 CPM All miles
$1,600 Gross Weekly Avg.
Home EVERY
2 – 4 WEEKS

No touch freight

10 CPM Safety/ productivity bonus

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

Detailed pay scale and benefits

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OTR DRY VAN TEAM

77 CPM All Miles
$3,850 Gross Weekly Avg.
Home every
2 – 4 weeks

No touch freight

5 CPM safety/ productivity bonus

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

Detailed payscale and benefits

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Flatbed

OTR FLATBED SOLO

65 CPM All Miles
$1,725 Gross Weekly Avg.
Home every
2 – 4 weeks

$2,500 sign-on bonus

5 CPM bonus on 11k+ miles monthly

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

Detailed pay scale and benefits

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OTR FLATBED TEAM

77 CPM All Miles
$3,850 Gross Weekly Avg.
Home every
2 – 4 weeks

$10,000 sign-on bonus

4 CPM bonus on 20k+ miles monthly

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

Detailed pay scale and benefits

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Hazmat & Doubles

OTR HAZMAT SOLO

60 CPM + 4 CPM All Miles
$1,725 Gross Weekly Avg.
Home every
2 – 4 weeks

No touch freight

10 CPM safety/ productivity bonus

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

Detailed pay scale and benefits

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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

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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

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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

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OWNER OPERATOR REGIONAL

75% of load All miles
$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

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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

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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

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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
Comfortable combo sleeper 579
Comfortable combo sleeper 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

Drive Your Career Forward with Trucking Jobs in Chicago

Put your commercial driver license to good use and build a stable, rewarding career. At HMD, we offer a variety of trucking jobs in Chicago and beyond — tailored to your experience, endorsements, and career goals. Enjoy competitive pay, steady miles, and real support from day one.

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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

OTR Dry Van Solo

May 2024

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

OTR Dry Van Teams

May 2024

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

OTR Flatbed Solo

May 2024

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 Flatbed Team

OTR Flatbed Team

May 2024

Nathan H. and Scott B.

Miles
22,750
Base CPM, $
0.77
Pay, $
17,518
Bonus pay CPM, $
0.04
Bonus pay, $
910
Load pay, $
640
Total, $
19,068

Brian M. and Nick A.

Miles
20,875
Base CPM, $
0.77
Pay, $
16,074
Bonus pay CPM, $
0.04
Bonus pay, $
835
Load pay, $
600
Total, $
17,509
OTR Hazmat Solo

OTR Hazmat Solo

May 2024

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

OTR Hazmat Teams

May 2024

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

OTR Doubles Teams

May 2024

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

Regional Dry Van Solo

May 2024

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.

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.

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