Regional Driving Jobs in Madison, WI — Now Hiring

As of September 2026, there are 15 regional driving openings in Madison, WI. Local pay ranges from $1,092 to $130,000/year. Listings are updated daily — many roles offer flexible hours and employee discounts.

Gannett

Newspaper Delivery Driver

Madison, WI

$1,092 - $2,184

Roadie

Box Truck Delivery Driver

Madison, AL

$3,825 - $6,630

Gannett

Newspaper Delivery Driver

Madison, AL

$1,296 - $2,592

Quest Diagnostics

Medical Courier Delivery Driver

Madison, WI

$2,800 - $4,200

Roadie

Box Truck Delivery Driver

Madison, WI

$4,950 - $8,580

Stevens Trucking

(Madison)Part-Time:Driver Opportunity

Madison, AL

$80,750 - $109,250

J.B. Hunt Intermodal

Urgent Hire in Madison:Driver Opportunity

Madison, AL

$71,250 - $90,250

Stevens Trucking

Earn Extra Cash:Driver Opportunity(Madison)

Madison, WI

$85,000 - $115,000

J.B. Hunt Intermodal

$85.75/hr Driver Opportunity-Madison(PT)

Madison, WI

$78,750 - $99,750

Foremost Transport

AL Career:Mobile Home Transport Driver-CDL A Oversize Load in Madison

Madison, AL

$90,000 - $120,000

Hot Shot Transportation Co.

Hot Shot Transportation Co. seeks Hot Shot Truck Driver-Owner Operator

Madison, AL

$85,000 - $130,000

Foremost Transport

Mobile Home Transport Driver-CDL A Oversize Load•Madison,WI•Foremost

Madison, WI

$90,000 - $120,000

Regional Driving Jobs in Madison — FAQ

How many regional driving jobs are open in Madison, WI?
There are currently 15+ regional driving in Madison, WI. New regional driving roles are added regularly — check this page for the latest openings.
How much do regional driving jobs pay in Madison?
Pay for regional driving in Madison varies by employer, equipment and how much time you spend away. Many positions offer flexible scheduling and employee discounts, and some include shift differentials for nights and weekends. Browse the listings above to see pay details for each opening.
Do these regional driving positions require experience in Madison?
Many regional driving positions in Madison require no prior experience, and most employers provide paid on-the-job training. Check individual listings for specific requirements.
How do I apply for regional driving jobs in Madison?
Browse the 15+ regional driving listings above, click on any position for full details including pay and shift times, then follow the application link to the employer. Most driver applications take about 10–20 minutes online.

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Other Driving Careers in Madison

Full-Time Driving Jobs in Madison

61 open positions

Delivery Driver Jobs in Madison

60 open positions

Part-Time Driving Jobs in Madison

43 open positions

CDL-A Truck Driving Jobs in Madison

32 open positions

CDL-B Driving Jobs in Madison

30 open positions

Weekend Driving Jobs in Madison

24 open positions

Local Driving Jobs (Home Daily) in Madison

20 open positions

Non-CDL Driving Jobs in Madison

16 open positions

Last updated: September 29, 2026