Flatbed CDL-A Truck Driver, Regional Routes - Milwaukee, WI

$1,021 - $2,280 per week

System Transport

Burlington, WI

AMERICA PROUD. FLATBED STRONG. DRIVE WITH SYSTEM TRANSPORT!
System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. You will be transporting important goods and materials such as glass, steel, aluminum, building materials, machinery, coils, and specialty metals. Join our team for competitive pay, excellent benefits, a great work-life balance, and become America Proud, Flatbed Strong with System Transport. Apply Today!

APPLICATION DEADLINE: 8/31/2026

CDL-A Flatbed Truck Driver Opportunities:

Driver Type: Experienced CDL-A Truck Drivers
Equipment Type: Flatbed
Route Type: Regional
Division: Division 290
Terminal: Kansas City, MO
Home Time: Off most weekends for a 34-hour reset

Compensation:

Weekly Pay: $1,021.00 - $2,280.00
Annual Pay: $53,092.00 - $118,560.00
Additional compensation: Tarp pay, stop pay, detention pay, safety bonuses, and more
Mileage rate: $0.65 - $0.71CPM, (depending on experience)
$1,800 transition package to help you settle in

Benefits:

Health, dental, and vision insurance
401(k) with company matching
Paid time off: Accrue 1 hour of sick time per 30 hours worked, then 1-9 years 80 hours PTO, 10+ years 120 hours PTO.
Life insurance, employee assistance programs, and much more!

Requirements:

Must have a valid Class A CDL
Must be 21 years of age or older
6+ months of driving experience
No more than 6 jobs in the last 3 years
1 year truck driving experience preferred, but not necessary
Clean driving record and drug test
Able to lift a 90-pound tarp onto a 5-foot platform (tested during orientation)

Additional Perks:

Rider Policy: Bring a rider aged 7+ after 90 days
Modern, well-maintained trucks with advanced safety features
24/7 road service support
Award-winning driver portal with real-time updates

Join System Transport and be part of the team that keeps America moving!

APPLICATION DEADLINE: 8/31/2026

System Transport is an Equal Opportunity Employer. We are committed to fair pay and equal opportunity for all employees.

Apply

Vacancy posted 16 days ago

Similar jobs that could be interesting for youBased on the Flatbed CDL-A Truck Driver, Regional Routes - Milwaukee, WI in Burlington, WI vacancy

CDL-A Flatbed Team Truck Driver - $0.63 to $0.70 per mile in Bassett, WI
...Company Driver | Flatbed Location: Bassett, WI Company: MK Trucking Pay: $0.63 to $0.70 per mile Route Type: otr, regional Start Date: ASAP About the Position OTR Flatbed... ...Requirements • Valid CDL Class A License • Minimum 1.5 Years of...
Hgv
Full time
Immediate start
Relocation package
MK Trucking
Bassett, WI
1 day ago
CDL-A Flatbed Team Truck Driver - $0.40 to $0.73 per mile in Bassett, WI
$3,400 per week
...Company Driver | Flatbed Location: Bassett, WI Company: Western Express Pay... ...to $0.73 per mile Route Type: otr, regional Start Date: ASAP... ...hook ** • Dependable trucks : Well-maintained fleet... ...THE TRAINING YOU NEED! (CDL-A required) INTERESTED...
Hgv
Full time
Immediate start
Western Express
Bassett, WI
1 day ago
CDL-A Flatbed Lease Purchase Driver in Kenosha, WI
$256k - $272k
...Company Driver | Flatbed Location: Kenosha, WI Company: CRST, The Transportation Solution... ...pay (inquire for details) Route Type: otr Start Date: ASAP... ...About the Position CDL-A Flatbed Independent Contractor Truck Drivers – Owner Operators and...
Hgv
Weekly pay
Full time
For contractors
Local area
Immediate start
Relocation package
CRST, The Transportation Solution
Kenosha, WI
1 day ago
CDL-A Flatbed Lease Purchase Driver - $3,600 to $8,200 per week in Bassett, WI
$3,600 - $8,200 per week
...Owner Operator | Flatbed Location: Bassett, WI Company: K1 TRANSFREIGHT INC... ...600 to $8,200 per week Route Type: otr Start Date:... ...great discounts - Physical truck and trailer insurance, non... ...truck is fixed) - Finding new drivers for you in case that you...
Hgv
Full time
Immediate start
K1 TRANSFREIGHT INC
Bassett, WI
1 day ago
CDL-A Company Driver - 6mo EXP Required - Regional - Flatbed - $106k per year - Decker
$106k
...Hiring Regional Midwest Flatbed Drivers. Now Hiring Regional Midwest Flatbed Drivers! Looking... ...home on weekends? At Decker Truck Line, we're hiring regional... ..., Smart TV, Satellite, Free Wi-Fi, CB Radio Driver Requirements ~ Valid CDL-A ~6 months CDL A Experience...
Hgv
Daily paid
Local area
Immediate start
Relocation package
Flexible hours
Decker
Lake Geneva, WI
8 hours ago
CDL A Flatbed Driver | Midwest Routes | $85K-$93K+
$85k - $93k
...Experience 1 Year Class A Employment Direct... ...We are hiring experienced CDL A Flatbed Drivers for Midwest regional routes offering strong annual... ...of: Green Bay, WI Appleton, WI Manitowoc... ...Manitowoc, WI Shawano, WI Milwaukee, WI Minneapolis, MN...
Weekly pay
Daily paid
Flexible hours
Road Warrior
Kenosha, WI
14 hours ago
CDL-A Refrigerated Truck Driver in Kenosha, WI
$1,000 - $1,100 per week
...Company Driver | Refrigerated Location: Kenosha, WI Company: Schneider... ...) Van Truckload truck driver Average... ...Experience: All CDL holders... ...Valid Class A Commercial Driver... ...choose Schneider Regional driving Variability... ...freight on different routes and in different...
Hgv
Hourly pay
Weekly pay
Full time
Apprenticeship
Immediate start
Relocation package
Schneider
Kenosha, WI
1 day ago
CDL-A Tanker Lease Purchase Driver - $3,000 to $7,000 per week in Bassett, WI
$3,000 - $7,000 per week
...Operator | Tanker Location: Bassett, WI Company: Sherman Brothers Heavy Trucking Pay: $3,000 to $7,000 per week Route Type: regional Start Date: ASAP About the... ...Hazmat Tanker Owner Operator Drivers to all 48 states. Owner operators...
Hgv
Full time
Immediate start
Sherman Brothers Heavy Trucking
Bassett, WI
1 day ago
Regional Flatbed CDL-A Driver: $903.55 - $2,199.05 per week. Off Most Weekends
$903.55 - $2,199.05 per week
...Job Description Job Description Flatbed CDL-A Driver, Multiple Route Options: $903.55 - $2,199.05 per week. System Transport is hiring CDL-A flatbed drivers for regional, local, dedicated, and OTR routes across the Western U.S. hauling steel, machinery, building...
Local area
Weekend work
System Transport
Burlington, WI
more than 2 months ago
CDL-A Regional Flatbed Driver - Higher Pay! $1,021.00 - $2,280.00 per week. Off Most Weekends
$1,021 - $2,280 per week
...Job Description Job Description Flatbed CDL-A Driver, Regional Route: $1,021.00 - $2,280.00 per week. YOU ASKED. WE LISTENED. SYSTEM TRANSPORT OFFERING HIGHER PAY FOR MIDWEST FLATBED DRIVERS! System Transport is hiring experienced CDL-A flatbed drivers for regional...
Weekend work
System Transport
Burlington, WI
more than 2 months ago
CDL-A Tanker Truck Driver - $1,500 to $2,000 per week in Bassett, WI
$1,500 - $2,000 per week
...Company Driver | Tanker Location: Bassett, WI Company: Sherman Brothers Heavy Trucking Pay: $1,500 to $2,000 per week Route Type: otr, regional Start Date: ASAP About the Position... ...Requirements ~ Class A license ~ X endorsement...
Hgv
Full time
Immediate start
Sherman Brothers Heavy Trucking
Bassett, WI
1 day ago
CDL-A Tanker Truck Driver - $1,500 to $2,000 per week in Bassett, WI
$1,500 - $2,000 per week
...Company Driver | Tanker Location: Bassett, WI Company: Sherman Brothers Heavy Trucking Pay: $1,500 to $2,000 per week Route Type: otr, regional Start Date: ASAP About the Position... .... Requirements ~ Class A license ~ X endorsement...
Hgv
Full time
Immediate start
Sherman Brothers Heavy Trucking
Bassett, WI
1 day ago
CDL-A Driver Jobs - Local, Regional & OTR Positions Hiring Now
$70k - $100k
CDL-A Truck Drivers Class A CDL Drivers – We'll Match You With Carriers... ...you're looking for local, regional, or over-the-road driving ,... ...Opportunities May Include Local routes with daily home time... ...mileage pay Dry van, reefer, flatbed, tanker, and specialized...
Hgv
Local area
Flexible hours
JobsTruckDriving.com
Pleasant Prairie, WI
1 hour ago
Class A CDL Company Driver - 6mo EXP Required - Regional - Flatbed - $106k per year - Decker
$106k
...Hiring Regional Midwest Flatbed Drivers. Now Hiring Regional Midwest Flatbed Drivers! Looking... ...home on weekends? At Decker Truck Line, we're hiring regional... ..., Smart TV, Satellite, Free Wi-Fi, CB Radio Driver Requirements ~ Valid CDL-A ~6 months CDL A Experience...
Hgv
Daily paid
Local area
Immediate start
Relocation package
Flexible hours
Decker
Kenosha, WI
19 hours ago
CDL-A Dry Van Truck Driver in Kenosha, WI
$1,450 - $1,900 per week
...Company Driver | Dry Van Location: Kenosha, WI Company: Terminal Transport, Inc.... ...inquire for details) Route Type: otr, regional Start Date: ASAP... ...well. No Northeast. Our CDL Drivers enjoy the following... ...school and a valid Class A CDL ~ Smart phone...
Hgv
Bi-weekly pay
Weekly pay
Full time
Immediate start
Terminal Transport, Inc.
Kenosha, WI
1 day ago
CDL-A Refrigerated Truck Driver - $1,610 to $2,000 per week in Bassett, WI
$1,610 - $2,000 per week
...Company Driver | Refrigerated Location: Bassett, WI Company: K&B Transportation Pay: $1,610 to $2,000 per week Route Type: dedicated, otr, regional Start Date: ASAP About the Position... ...to join them? If you have a CDL A and 1 years experience call...
Hgv
Full time
Immediate start
K&B Transportation
Bassett, WI
1 day ago
CDL A Local Walking Floor Driver in Milwaukee, WI
$30 per hour
...Reworld is hiring a CDL A local walking floor driver in Milwaukee, WI. Drivers are responsible for the safe transportation of non‑hazardous materials between... ...Paid parental leave Pet insurance Home time, Route & Schedule Home time: Home daily (weather and...
Hourly pay
Weekly pay
Daily paid
Local area
Flexible hours
Night shift
Reworld
Kenosha, WI
2 days ago
CDL-A Refrigerated Truck Driver - $0.65 to $0.82 per mile in Bassett, WI
$1,886 per week
...Company Driver | Refrigerated Location: Bassett, WI Company: K&B Transportation Pay... ...5 to $0.82 per mile Route Type: otr Start Date... ...: Traditional Midwest Regional. Start at 70 CPM. Drivers... ...to Orientation Have a Class A CDL and 1 years OTR experience...
Hgv
Full time
Immediate start
K&B Transportation
Bassett, WI
1 day ago
CDL-A Refrigerated Truck Driver - $1,725 to $2,200 per week in Bassett, WI
$1,725 - $2,200 per week
...Company Driver | Refrigerated Location: Bassett, WI Company: K&B Transportation... ...$2,200 per week Route Type: dedicated, otr, regional Start Date: ASAP... ...that we don’t get to by truck, we fly you home for... ...join them? If you have a CDL A and 1 years...
Hgv
Full time
Immediate start
K&B Transportation
Bassett, WI
1 day ago
CDL-A Dry Van Truck Driver in Kenosha, WI
$650 per month
...Company Driver | Dry Van Location: Kenosha, WI Company: Terminal Transport, Inc. Pay: Competitive weekly pay (inquire for details) Route Type: otr, regional Start Date: ASAP About the Position Regional Drivers Needed ~ Consistent + Flexible...
Hgv
Weekly pay
Full time
Immediate start
Relocation package
Flexible hours
Terminal Transport, Inc.
Kenosha, WI
1 day ago
CDL-A Dry Van Truck Driver in Bassett, WI
$650 per month
...Company Driver | Dry Van Location: Bassett, WI Company: Terminal Transport, Inc. Pay: Competitive weekly pay (inquire for details) Route Type: otr, regional Start Date: ASAP About the Position OTR Drivers Needed Consistent + Flexible home...
Hgv
Weekly pay
Full time
Immediate start
Flexible hours
Night shift
Terminal Transport, Inc.
Bassett, WI
1 day ago
CDL A Regional Dedicated Tanker Driver in Chicago, IL
$1,700 - $2,000 per week
...Quality Carriers is looking for a CDL A regional dedicated tanker driver in Chicago, IL.... ...Largest Liquid Bulk Chemical Truck Fleet in North America. At... ...Seating: No Home Time, Route, & Schedule... ...Operating lanes include: IN, IL, WI, MI, OH, MO, MN, IA, PA, KS...
Hgv
Weekly pay
Temporary work
Relocation
Relocation package
Flexible hours
Weekend work
Quality Carriers
Kenosha, WI
1 day ago
CDL-A Refrigerated Truck Driver - $1,400 to $2,000 per week in Bassett, WI
$1,400 - $2,000 per week
...Company Driver | Refrigerated Location: Bassett, WI Company: Van Eerden Trucking Company Pay: $1,400 to $2,000 per week Route Type: dedicated, regional Start Date: ASAP About the Position Regional run in the Great Lakes Area. We have...
Hgv
Daily paid
Price work
Full time
Temporary work
Immediate start
Van Eerden Trucking Company
Bassett, WI
1 day ago
CDL Class A Regional Driver
$80k - $100k
...CDL Class A Regional Driver GFI Midwest - Kenosha, WI 53144 Start Date 05/26/2026 End Date 09/28/2026 Overview Salary Range $8... ...Program). Modern equipment, late-model trucks with XM Radio and Bluetooth. Dedicated routes, consistent schedules. Family-owned...
Hgv
Full time
Temporary work
Shift work
Night shift
Gourmet Foods International
Kenosha, WI
3 days ago
OTR Flatbed Company driver (W-2) Job in Kenosha, WI by HMD Trucking
$25 per hour
...Requirements ~1 year of CDL-A OTR experience ~6 months of flatbed experience ~ No DUI/... ...loaded miles (company drivers only) ~ Extra Stops: $... ...Join HMD Trucking’s Kenosha, WI flatbed fleet for high-earning cross-country routes. What You'll Do:...
Hgv
Hourly pay
Full time
Second job
Relocation package
Flexible hours
Night shift
HMD Trucking
Kenosha, WI
1 day ago
Truck Driver CDL A Regional Solo
$1,630 per week
...Description Ryder is hiring a Class A CDL Truck Driver in Harvard, IL offering... ...nights per Week Overnights for Route in Ryder Booked Hotel Paid... .... Deliver SOLO?To:?IL, WI, IA, OH, MI, IN, KS, NE, MN, ND, SD & KY Route: Regional Tractor Type: Day Cab Trailer...
Hgv
Weekly pay
Daily paid
Full time
Relocation package
Monday to Friday
Shift work
Night shift
Ryder
Burlington, WI
4 days ago
CDL-A Refrigerated Truck Driver in Twin Lakes, WI
$1,250 - $1,800 per week
...Company Driver | Refrigerated Location: Twin Lakes, WI Company: Marten Transport Pay: Competitive weekly pay (inquire for details) Route Type: regional Start Date: ASAP About the Position CDL-A Truck Drivers- Join a 2-Time TCA Elite Fleet...
Hgv
Weekly pay
Full time
Immediate start
Relocation package
Flexible hours
Marten Transport
Twin Lakes, WI
1 day ago
CDL-A Refrigerated Truck Driver in Pleasant Prairie, WI
$1,350 - $1,650 per week
...Company Driver | Refrigerated Location: Pleasant Prairie, WI Company: Marten Transport Pay: Competitive weekly... ...pay (inquire for details) Route Type: regional Start Date: ASAP About the Position CDL-A Truck Drivers- Join a 2-Time TCA...
Hgv
Weekly pay
Full time
Immediate start
Relocation package
Flexible hours
Marten Transport
Pleasant Prairie, WI
1 day ago
CDL-A Dry Van Truck Driver in Kenosha, WI
$95k - $105k
...Company Driver | Dry Van Location: Kenosha, WI Company: CRST, The Transportation... ...inquire for details) Route Type: regional Start Date: ASAP... ...America. We are looking for a CDL Class A Driver to drive... ...Automatic Transmissions trucks ~ Driver will be assisting...
Hgv
Weekly pay
Full time
Seasonal work
Local area
Immediate start
Relocation package
CRST, The Transportation Solution
Kenosha, WI
1 day ago
CDL A Regional Dry Van Drivers in the Midwest
$1,200 - $1,800 per week
...Transport is hiring full-time CDL A Regional Dry Van Drivers in the Midwest. At River City Transport... ...upon approval Take your truck home program Home Time, Route, & Schedule Home time:... ...City is hiring drivers inIA, KS, MO, IL, IN, WI, OH, & PA...
Hgv
Hourly pay
Weekly pay
Full time
RIVER CITY TRANSPORT LLC
Kenosha, WI
14 hours ago

Do you want to receive more vacancies?

Subscribe and receive similar vacancies to Flatbed CDL-A Truck Driver, Regional Routes - Milwaukee, WI. Be the first to apply!