Driving Jobs in Winona, MN — Open Positions

As of May 2026, there are 40+ open driving positions in Winona, MN. Current pay ranges from $14 to $135,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Yard Jockey. New roles are posted daily — listings on this page are verified and updated regularly.

Auto Logistics Pros

Winona Contractor Independent Contractor Driver-Auto Parts Courier

Winona, MN

$2,800 - $4,800

Granite Construction

Winona Career:CDL B Water Truck Driver-Construction Site Dust Control

Winona, MN

$26 - $32

Local Merchant Delivery Network

Independent Contractor Driver-Early Morning Bakery/floral-Winona,MN

Winona, MN

$2,400 - $4,200

Postmates

Winona Contractor Same-day Delivery Driver | Hiring

Winona, MN

$3,456 - $5,832

Clean Harbors

Immediate Opening in Winona for a CDL B Vacuum Truck Driver-Industrial

Winona, MN

$25 - $34

Heavy Freight Logistics

Work in Winona:Independent Contractor Driver-Cargo Van / Box Truck

Winona, MN

$5,000 - $8,500

Amazon Flex

Recruiting in Winona:Delivery Driver-Independent Contractor | Hiring

Winona, MN

$18 - $25

Quest Diagnostics

Winona Full-time Opening:Delivery Driver-Medical Courier

Winona, MN

$20 - $26

Matheson Postal Services

Matheson Postal Services is hiring a USPS Mail Haul Truck Driver-CDL A

Winona, MN

$78,400 - $100,800

FedEx Ground

Winona Delivery Driver-Package Handler(Full-time)-Fedex Ground

Winona, MN

$21 - $26

FedEx Custom Critical

Expedited Sprinter Van Driver-Time Critical

Winona, MN

$75,000 - $135,000

DoorDash

Join Doordash in Winona as a Delivery Driver-Food Delivery Part Time

Winona, MN

$15 - $22

Driving Jobs in Winona — FAQ

How many driving jobs are available in Winona, MN right now?
There are currently 40+ open driving positions in Winona, MN. 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 Winona?
Driving job pay in Winona 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 Winona?
Yes. Many delivery driver, courier, and DSP positions in Winona 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 Winona?
Driving jobs in Winona 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 Winona?
Benefits vary by employer, but many driving positions in Winona 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 Winona?
Your take-home pay as a driver in Winona 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 Winona?
Yes, many driving positions in Winona 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 40+ listings above and apply directly.

Last updated: May 13, 2026