Driving Jobs in Madison, WI — Now Hiring

As of May 2026, there are 400+ open driving positions in Madison, WI. Current pay ranges from $500 to $10,000 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Madison, WI

$2,300 - $4,600

Lyft

Lyft(Madison)Hiring:XL Rideshare Driver | Apply Now

Madison, WI

$4,000 - $6,500

Suburban Delivery Network

Earn Extra Cash:Driver Opportunity(Madison)

Madison, AL

$2,800 - $4,800

Uber

$3.7k-$6k/Month Uberxl Driver job in Madison | Hiring

Madison, WI

$3,680 - $5,980

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Madison, WI

$4,000 - $7,000

Wholesale Transit Partners

[Part-Time] Driver Opportunity-Madison

Madison, AL

$3,040 - $5,225

Grubhub

Madison Part-Time:Night Shift Courier(Now Hiring) | Part Time Job

Madison, AL

$2,800 - $4,800

Amazon Delivery Service Partners

Amazon DSP Delivery Van Driver(Contract)|Madison

Madison, AL

$3,400 - $4,800

Uber

Apply Now:Night Shift Rideshare Driver in Madison | Hiring

Madison, WI

$3,200 - $5,500

Uber

Suburban Route Ubereats Driver(Contract)-Madison,WI

Madison, WI

$2,400 - $4,200

Morning Express Couriers

Evening Role:Driver Opportunity(Madison)

Madison, MS

$2,200 - $3,800

Grubhub

Part-Time Job Madison at Grubhub | Part Time Job

Madison, WI

$2,800 - $4,800

Driving Jobs in Madison — FAQ

How many driving jobs are available in Madison, WI right now?
There are currently 400+ open driving positions in Madison, WI. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Madison?
Driving job pay in Madison varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Madison?
Yes. Many delivery driver, courier, and DSP positions in Madison require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Madison?
Driving jobs in Madison offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Madison?
Benefits vary by employer, but many driving positions in Madison offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Madison?
Your take-home pay as a driver in Madison depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Madison?
Yes, many driving positions in Madison are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 400+ listings above and apply directly.

Last updated: May 04, 2026