Driving Jobs in Madison, WI — Now Hiring

As of May 2026, there are 540+ open driving positions in Madison, WI. Current pay ranges from $440 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.

Lyft

Event Rideshare Driver Position in Madison | Hiring

Madison, WI

$2,800 - $5,000

Grubhub

Local Part-Time Part-time Driver(lunch Rush)Job – Madison | Part

Madison, WI

$800 - $1,800

Uber

Madison Contractor Role:Suburban Route Ubereats Driver

Madison, WI

$2,112 - $3,696

Secure Document Couriers

Madison Independent Contractor Driver-Night Shift Legal/document

Madison, AL

$3,219 - $5,750

Regional Auto Dealership Group

Madison OEM Dealership Auto Parts Delivery Driver with $3k-$4.5k/Month

Madison, WI

$3,000 - $4,500

Corporate Catering Couriers

Apply Now:Independent Contractor Driver-Catering Logistics in Madison

Madison, WI

$4,024 - $6,899

City Waste Solutions

Evening/Weekend Residential Waste & Recycling Route Driver(Madison)

Madison, AL

$4,500 - $6,500

Grubhub

Weekend Grubhub Delivery Professional

Madison, WI

$2,002 - $3,458

Instacart

Urban E-Bike Instacart Courier

Madison, WI

$2,800 - $5,040

CareDrop Couriers

Pharmacy Delivery Courier (Last-Mile Healthcare)

Madison, WI

$3,150 - $4,725

Uber

Madison Contractor EV Rideshare Driver | Hiring

Madison, AL

$3,000 - $5,500

United Parcel Service (UPS)

Madison Contract:UPS Package Delivery Driver

Madison, AL

$4,000 - $8,000

Driving Jobs in Madison — FAQ

How many driving jobs are available in Madison, WI right now?
There are currently 540+ 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 540+ listings above and apply directly.

Last updated: May 08, 2026