OTR Dry Van Solo
$1,625Gross Weekly Avg.
65 CPMAll Miles
Every 2–4 weeksHome time
$2,500 sign-on bonus
10 CPM Safety/ productivity bonus
Health, dental, vision, 401k, paid time off
Truck Driving 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
Enter your ZIP code below to see which CDL A driver jobs are available in your area.
Dry Van
Regional Dry Van Solo
$1,260Gross Weekly Avg.
70 CPMAll miles
WeeklyHome time
$2,500 sign-on bonus
Health, dental, vision, 401k, paid time off
Orientation, clean inspection pay, and referral bonus
OTR Dry Van Team
$3,850Gross Weekly Avg.
82 CPM *All Miles
Every 2–4 weeksHome time
$10,000 sign-on bonus
5 CPM safety/ productivity bonus
Health, dental, vision, 401k, paid time off
* When 95% service is achieved
Flatbed
OTR Flatbed Solo
$1,750Gross Weekly Avg.
70 CPMAll miles
Every 2 – 4 WeeksHome time
$5,000 sign-on bonus
10 CPM safety/ productivity bonus
Health, dental, vision, 401k, paid time off
Hazmat & Doubles
OTR Hazmat Solo
$1,725Gross Weekly Avg.
65 CPMAll miles
+2 CPMWhen hauling hazmat
Every 2–4 weeksHome time
$2,500 sign-on bonus
10 CPM safety/ productivity bonus
Health, dental, vision, 401k, paid time off
OTR Hazmat Team
$4,050Gross Weekly Avg.
82 CPM *All miles
+2 CPMWhen hauling hazmat
Every 2–4 weeksHome time
$10,000 sign-on bonus
5 CPM safety/ productivity bonus
Health, dental, vision, 401k, paid time off
* When 95% service is achieved
OTR Doubles Team
$4,050Gross Weekly Avg.
82 CPM *All miles
+2 CPMWhen hauling doubles
Every 2–4 weeksHome time
$10,000 sign-on bonus
5 CPM safety/ productivity bonus
Health, dental, vision, 401k, paid time off
* When 95% service is achieved
Lease & Owner Operator
Owner Operator OTR
$5,625Gross Weekly Avg.
75%Of load
Every 2–4 weeksHome time
$100 Clean inspection bonus
Referral bonus of $2,000
All paperwork done by HMD
Owner Operator Regional
$4,500Gross Weekly Avg.
75%Of load
WeeklyHome time
$100 Clean inspection bonus
Referral bonus of $2,000
All paperwork done by HMD
Dry Van Lease Purchase
NoCredit check
75%Of load
Walk awayOption
Fuel discount program available
Multiple down payment options including 0 down
24/7 on the road support
Flatbed Lease Purchase
NoCredit check
75%Of load
Walk awayOption
$0 buyout
Multiple down payment options including 0 down
Fully equipped trailer in lease
Trucks You'll Drive
Our fleet keeps growing. Today, HMD Trucking operates over 650 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.
HMD Trucking semi trucks come with the following features:
Peterbilt
Spacious, high-roof cabin
Inverter
Powerful diesel APU
Minifridge
Automatic
Removable rider seat
Comfortable combo sleeper
HMD Trucking Company started as a family business in Chicago, Illinois, back in 1998
Today, we operate a fleet of over 650+ 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.
See how much you can earn at HMD
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. Ready to join? Apply now for truck driver jobs in Chicago, Illinois — it only takes a minute.
Apply nowRegional Dry Van Solo
May 2026Harold A.
Miles Dry Van10,490
Base CPM$0.70
Base Pay$7,343
Total$7,343
Austin P.
Miles Dry Van9,080
Base CPM$0.70
Base Pay$6,356
Total$6,356
Ryan N.
Miles Dry Van9,790
Base CPM$0.70
Base Pay$6,853
Total$6,853
What makes truck driving job at HMD enjoyable
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
We’re a top-rated transportation company serving routes across the United States. We regularly have open truck driver jobs in Chicago, IL, for experienced drivers.
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, well-maintained tractor trailers, and real support from day one. Build your commercial driving career with HMD.
Recruiting: 888 215 8523
By clicking "Apply Now", you agree that HMD Trucking may contact you by phone and email regarding your driver application. You also agree to our Terms of Service and Privacy Policy.
HMD Trucking Blog
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FMCSA English Requirement: Bracing for Stricter DOT Enforcement
Discover how the new FMCSA English requirement turns language checks into out-of-service violations and has impacted over 10,000 drivers in 2026.
The 2026 Broker Transparency Rule: A Battle for Honest Freight Loads
Learn how the 2026 FMCSA broker transparency rule aims to protect small fleets from income theft and create a fairer market.
Navigating the FMCSA Motus Registration System and the End of MC Numbers
Learn how the FMCSA Motus registration system uses USDOT suffixes to simplify compliance and stop chameleon carrier fraud.
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