Driving Jobs in Madison, WI — See Openings

As of April 2026, there are 510+ open driving positions in Madison, WI. Current pay ranges from $425 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Task & Dash Couriers

On-Demand Local Courier (Gig Economy)

Madison, WI

$1,900 - $3,800

Uber

Madison Job:Suburban Route Ubereats Driver(Contractor) | Hiring

Madison, AL

$2,400 - $4,200

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Madison, AL

$2,750 - $4,950

Shipt

(Madison)Part-Time:Evening & Night Shift Courier

Madison, AL

$2,800 - $4,800

Instacart

Urban E-Bike Instacart Courier

Madison, WI

$2,625 - $4,725

Urban Pedal Logistics

Madison Independent Contractor Driver-Urban E-bike/scooter

Madison, AL

$2,300 - $4,140

Corporate Catering Couriers

Recruiting:Independent Contractor Driver-Catering Logistics in

Madison, WI

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver-Urban E-bike/scooter Courier-Madison,WI

Madison, WI

$2,500 - $4,500

Corporate Catering Couriers

Apply Now:Independent Contractor Driver-Catering Logistics in

Madison, WI

$4,024 - $6,899

United States Postal Service

USPS Commercial Box Truck Driver (MVO)

Madison, AL

$5,175 - $7,474

Secure Document Couriers

Secure Document Couriers seeks Independent Contractor Driver-Night

Madison, AL

$3,136 - $5,600

Lyft

Premium Rideshare Driver•Madison,WI•Lyft | Hiring

Madison, WI

$4,500 - $7,500

Driving Jobs in Madison — FAQ

How many driving jobs are available in Madison, WI right now?
There are currently 510+ 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 510+ listings above and apply directly.

Last updated: April 17, 2026