Driving Jobs in Winona, MN — See Openings

As of September 2026, there are 20+ open driving positions in Winona, MN. Current pay ranges from $1,200 to $9,180 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Winona, MN

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Winona, MN

$2,700 - $4,860

On-Demand Tasks Network

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

Winona, MN

$2,100 - $4,200

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Winona, MN

$5,400 - $9,180

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winona, MN

$2,800 - $5,000

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winona, MN

$2,592 - $4,536

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Winona, MN

$3,850 - $6,600

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winona, MN

$3,449 - $6,324

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Winona, MN

$2,380 - $4,080

United Parcel Service (UPS)

UPS Package Delivery Driver

Winona, MN

$4,000 - $7,500

Domino's Pizza

Urgent Hire:Pizza Delivery Driver in Winona,MN | Hiring

Winona, MN

$2,500 - $4,200

Amazon DSP

Winona Delivery Driver($3.9k-$5.3k/Month) | Hiring

Winona, MN

$3,850 - $5,280

Driving Jobs in Winona — FAQ

How many driving jobs are available in Winona, MN right now?
There are currently 20+ 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 20+ listings above and apply directly.

Last updated: September 11, 2026