Driving Jobs in Winona, MN — Open Positions

As of October 2026, there are 50+ open driving positions in Winona, MN. Current pay ranges from $14 to $85,000 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.

Roadie

Join Roadie in Winona as a Box Truck Delivery Driver | Hiring

Winona, MN

$5,175 - $8,970

DoorDash

Weekend Shift:Driver Opportunity-Winona

Winona, MN

$2,400 - $4,200

United States Postal Service

Winona,MN:Class A CDL Tractor Trailer Operator-USPS at United States

Winona, MN

$5,500 - $8,000

Amazon Flex

Driver Opportunity(Part-Time)@ Amazon Flex-Winona

Winona, MN

$4,500 - $7,500

GoPuff

Urgent Hire in Winona:Driver Opportunity

Winona, MN

$2,800 - $4,500

Schneider National

$74.50/hr Driver Opportunity-Winona(PT)

Winona, MN

$70,000 - $85,000

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winona, MN

$3,449 - $6,324

Amazon Flex

Driver Opportunity(Part-Time)@ Amazon Flex-Winona

Winona, MN

$18 - $25

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winona, MN

$2,800 - $5,000

Grubhub

Urgent Hire in Winona:Driver Opportunity

Winona, MN

$3,150 - $5,145

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Winona, MN

$5,400 - $9,180

XPO Logistics

Driver Opportunity needed in Winona(Apply Now)

Winona, MN

$22 - $28

Driving Jobs in Winona — FAQ

How many driving jobs are available in Winona, MN right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: October 03, 2026